OXAZOLIDINONES AND THEIR USE AS ANTIINFECTIVES

Abstract: Compounds of formula (1) wherein: R6 is substituted thioacyl, aminocarbonyl, alkoxycarbonyl, aminothiocarbonyl, alkoxythiocarbonyl, alkylthio(carbonyl), or alkylthio(thiocarbonyl); R7 is aryl or heteroaryl; and R8-R9 are specified substituents; are useful in treating or preventing an infectious disorder in a human or other animal subject.

Description: OXAZOLIDINONES AND THEIR USE AS ANTIINFECTIVES OXAZOLIDINONE COMPOUNDS AND METHODS OF PREPARATION AND USE THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of provisional U S patent application Serial No 60/146,012, filed July 28, 1999 FIELD OF THE INVENTION The present invention is directed to oxazolidmones. oxazohd one compositions, and methods for their preparation and use BACKGROUND ART Oxazolidmones are compounds where an amine group and a hydroxyl group on adjacent carbon atoms have been cychzed to form a 5-membered ring containing a carbonyl group Certain oxazolidmones have been shown to exhibit a variety of biological activities For example, some oxazolidmones are inhibitors of monoamine oxidase-B, an enzyme implicated in Parkinson's disease See, for example. Ding et al , J Med Chem 36 3606-3610 (1993) Scientists have reported that certain oxazohdmone derivatives exhibit beneficial antibacteπal effects For instance, N-[3-[3-fluoro-4-(morphohn-4- yl)phenyl]2-oxooxazohdιn-5(s)-ylmethyl] acetamide (below) has been reported to be useful for the treatment of bacterial infections Lizondo et al , Drugs of the Future, 21 1116-1123 (1996) A ten step synthesis of oxazohdmone antibiotics has been described U S Patent No 5,547,950 A four step synthesis of the antibacterial compound U- 100592 also has been reported Schauss et al , Tetrahedron Letters, 37 7937-7940 ( 1996) A five step preparation of enantiomeπcally pure cis- and trons-N- (propιonyl)hexahydrobenzoxazohdιn-2-ones further was reported De Parrodi et al , Tetrahedron Asymmetry, 8 1075-1082 (1997) The synthesis of the oxazohdmone antibacterial agent shown below has been reported Wang et al , Tetrahedron, 45 1323-1326 (1989) This oxazohdmone was made using a process that included the reaction of an aniline with glycidol to provide an ammo alcohol, and the diethylcarbonate mediated cychzation of the amino alcohol to afford an oxazohdmone The synthesis of oxazohdmone antibacterial agents, including the compound shown below has been reported U S Pat No 4,705,799 The process used to make the compound shown below included a metal mediated reduction of a sulfonyl chloride to provide a sulfide The synthesis of oxazohdmone antibacteπal agents, including the pyπdyl compound shown below has been reported U S Patent No 4,948,801 The process used included an organometalhc mediated coupling of an organotin compound and an aryl iodide Other reports of syntheses of oxazohdmone compounds are described in DE 196 01 264 A l. EP 0 789 026 Al. DE 196 04 223 A l . EP 0 738 726 A l and PCT WO 98/54161 The synthesis of oxazohdmone compounds also is described in U S Patent Application Serial No 09/012.535, filed January 23. 1998. U S Patent Application Serial No 09/086.702, filed May 28. 1998. U S Patent Application Serial No 09/235.771. filed January 22, 1999. and PCT US99/01318. filed January 22. 1999, the disclosures of which are incorporated herein by reference in their entirety SUMMARY OF INVENTION Provided are oxazolidmones, compositions compπsing oxazolidmones, as well as methods of their synthesis and use Also provided are compositions for the treatment or prevention of an infectious disorder compπsing an effective amount of any oxazohdmone compound disclosed herein and a pharmaceutically acceptable earner Methods are provided of treating or preventing an infectious disorder in a human or other animal subject, compπsing admi steπng to the subject an effective amount of any oxazohdmone compound disclosed herein BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 shows the structure of some exemplary thiocarbonyl oxazohdmone compounds Figure 2 shows another embodiment of structures of some exemplary thiocarbonyl oxazohdmone compounds Figure 3 shows further embodiments of the structure of some exemplary thiocarbonyl oxazohdmone compounds Figure 4 shows further embodiments of the structure of some exemplary thiocarbonyl oxazohdmone compounds Figure 5 shows further embodiments of the structure of some exemplary thiocarbonyl oxazohdmone compounds Figure 6 shows structures of some exemplary oxazohdmone compounds of formula 2 DETAILED DESCRIPTION Definitions As used herein, the terms and phrases have the meanings and definitions known in the art. Some of the more commonly used phrases are described in more detail below "Combinatorial library " or '"array' * is an intentionally created collection of differing molecules which can be prepared synthetically and screened for biological activity in a variety of different formats (e.g., hbraπes of soluble molecules, hbraπes of molecules bound to a solid support). Typically. combinatorial libraries contain between about 6 and two million compounds In one embodiment, combinatorial hbraπes contain between about 48 and 1 million compounds. For example, combinatorial libraries may contain between about 96 and 250.000 compounds. In another embodiment, combinatorial hbraπes may contain about 40 to 100 compounds "Alkyl" refers to a cyclic, branched or straight chain chemical group containing only carbon and hydrogen, such as methyl, pentyl. and adamantyl. Alkyl groups can either be unsubstituted or substituted with one or more substituents, e.g., halogen, alkoxy. acyloxy, amino, hydroxyl, mercapto. carboxy. benzyloxy. phenyl, and benzyl. Alkyl groups can be saturated or unsaturated (e.g.. containing -C=C- or -C≡C- subunits). at one or several positions Typically, alkyl groups will compπse about 1 to 12 carbon atoms, for example about 1 to 10, or about 1 to 8 carbon atoms "Heteroalkyl" refers to a cyclic, branched or straight chain chemical group containing carbon, hydrogen and at least one heteroatom. The heteroatom will be typically nitrogen, oxygen or sulfur. Heteroalkyl groups can either be unsubstituted or substituted with one or more substituents. e.g.. halogen, alkoxy, acyloxy. amino. hydroxyl. mercapto. carboxy, benzyloxy, phenyl. benzyl Where the heteroalkyl group contains a nitrogen atom, the nitrogen atom can be pπmary, secondary, tertiary, quaternary or can be in vaπous forms such as an amide or sulfonamide. Heteroalkyl groups can contain one or more unsaturated (e g . - C=C- or -C≡C-) subunits Typically, heteroalkyl groups will compπse 1 to 12 atoms, for example 1 to 8, or 1 to 4 carbon atoms "Aryl" refers to a monovalent unsaturated aromatic carbocychc group having a single πng (e g phenyl). multiple rings (e g biphenyl). or multiple condensed rings (e g naphthyl or anthryl) Aryl groups can be optionally unsubstituted or substituted with amino. hydroxyl. alkyl, heteroalkyl, alkoxy. halo, mercapto and other substituents Typically, the aryl group is a substituted single πng compound For example, the aryl group is a substituted phenyl πng "Heteroaryl" refers to a monovalent unsaturated aromatic carbocychc group having a single πng (e g , pyπdyl or furyl) or multiple condensed πngs (e g , lndoliz yl or benzothienyl) and having at least one heteroatom within the πng The heteroatom in the ring is preferably nitrogen, oxygen or sulfur Heteroaryl groups can be optionally unsubstituted or substituted with amino. hydroxyl. alkyl, heteroalkyl. alkoxy, halo, mercapto and other substituents In one embodiment, the heteroaryl group is substituted "Electron withdrawing group" refers to a substituent that draws electrons to itself more than a hydrogen atom would if it occupied the same position in a molecule This definition according to field effect is discussed in March. "Advanced Organic Chemistry." 3d Edition, pp 16-17. Wiley-Interscience. New York It should be contrasted with a definition based on resonance effects Examples of electron withdrawing groups include -NR , -COOH. -OR, -SR. -F, -COR. -CI, -SH. -NO 2 , -Br, -NH 2 , -S0 2 R, -I. -OH, -CN, -C=CR 2 , where R is alkyl. heteroalkyl. aryl or heteroaryl "Chemical module" refers to a general class of molecules that can be incorporated into a combinatoπal library at a discrete step in the library synthesis For example, thiols are chemical modules that can be coupled to a substrate, where the synthetic route employs a nucleophile to displace a solid support bound leaving group, isocyanates are chemical modules that can be coupled to a substrate, where the synthetic route employs an electrophile to react with a solid support bound amine Chemical modules can contain tens, hundreds or thousands of different individual members "Protecting group ' refers to a chemical group that exhibits the following characteristics ( 1 ) reacts selectively with the desired functionality in good yield to give a protected substrate that is stable to the projected reactions for which protection is desired. 2) is selectively removable from the protected substrate to yield the desired functionality, and 3) is removable good yield by reagents compatible with the other functional group(s) generated in such protection reactions Examples of protecting groups can be found in Greene et al (1991) Protective Groups in Organic S\nthesιs, 2nd Ed (John Wiley & Sons, Inc . New York) "Biologically active oxazohdmone compounds " or "bioactive oxazohdmone compounds " refers to an oxazohdmone compound that exhibits biological activity For instance, a biologically active oxazohdmone can inhibit the interaction between an enzyme or receptor and its respective substrate(s) or endogenous hgand(s). or inhibit cell growth of a microorganism, by about at least 15% at a solution concentration of 10 molar or lower (l e . it has inhibitory activity) For example, the biologically active oxazohdmone will inhibit such processes at solution concentrations of about 10 "4 M or lower, or 10 ^ M or lower, or, e g . of about 10 6 M or lower Oxazolidmones Provided are oxazolidmones, and compositions compπsing oxazolidmones, as well as methods for their synthesis, for example, by solid phase synthesis methods, and methods for their use A variety of oxazolidmones are provided that optionally have biological activity, such as antimicrobial activity In one embodiment, oxazolidmones 1 are provided wherein in one embodiment Re is thioacyl. aminocarbonyl. alkoxycarbonyl. aminothiocarbonyl. alkoxythiocarbonyl. alkylthιo(carbonyl), or alkylthιo(thιocarbonyl), R 7 is aryl or heteroaryl, R 8 is alkyl (e.g., C C alkyl). alkenyl (e.g .C 1 -C 7 alkenyl), alkynyl (e g.. C,-C 7 alkynyl). NR. O. S. C(=0)NR. NRC(=O). C(=O). C(=O)O. OC(=0), OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S). C(=S), C(=S)O. OC(=S). OC(=S)NR. NRC(=S)0, S(=O). S0 2 , S0 2 NR, NRSO : , NRCONR'. NRC(=S)NR' , or (CH 2 ) n O. wherein n = 0-20. e.g., 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl. aryl or heteroaryl: and RQ is hydrogen. OH. OR". SR". NR"R'" . alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R"' are independently H. alkyl, heteroalkyl. aryl or heteroaryl. In one embodiment of the compounds of formula 1. Rg is NR. S, C(=O)NR, NRC(=0), C(=0)0. OC(=0), OC(=0)NR. C(=S)NR. NRC(=S), OC(=S)NR. NRC(=S)0. or NRC(=S)NR'. wherein R and R ' are independently H, alkyl. heteroalkyl. aryl or heteroaryl; and R 9 is hydrogen. OR". SR", NR"R'". alkyl, aryl. or heteroaryl. wherein each R" and R'" are independently H, alkyl. aryl or heteroaryl. In one embodiment of the compounds of formula 1, R is a thioacyl group. Exemplary thioacyl groups include C(=S)CH . C(=S)CH 2 CH 3 , C(=S)H. and C(=S)cyclopropyl. Examples of oxazohdmone compounds are provided in Figures 1-5 Figure 6 further provides examples of oxazohdmone compounds of formula 2 In one embodiment of the compounds of formula 1, Rg is not aryl. heteroaryl, morphohno, piperazino, thiomorphohno, mdolino. or thiopyrano In one preferred embodiment. R7 and Rg are not directly bonded. Also provided are compounds of formula 3 wherein in one embodiment: R 7 is aryl or heteroaryl: Rg is alkyl (e.g., C 1 -C7 alkyl), alkenyl (e.g., C|-C 7 alkenyl). alkynyl (e.g.. as C1-C7 alkynyl). NR. O. S. C(=0)NR. NRC(=O). C(=0). C(=0)O. OC(=0). OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S), C(=S). C(=S)O. OC(=S). OC(=S)NR. NRC(=S)0, S(=O). S0 2 , S0 2 NR. NRS0 2 . NRCONR'. NRC(=S)NR ' , or (CH 2 ) n O, wherein n = 0-20. e.g.. 0-6. and wherein each R and R' are independently H. alkyl, heteroalkyl, aryl or heteroaryl; R 9 is hydrogen. OH, OR". SR", NR"R"\ alkyl. aryl, heteroalkyl. or heteroaryl, and wherein each R" and R' " are independently H, alkyl. heteroalkyl, aryl or heteroaryl; and Rio is H. alkyl, heteroalkyl. aryl or heteroaryl. In one embodiment of the compounds of formula 3. R J O is H; alkyl such as Cj- 4 alkyl; substituted alkyl such as - alkyl substituted with 1-3 F, 1-2 CI. CN, N0 2 or COOC 1 -C4 alkyl; or R, 0 is a C 3 - 6 cycloalkyl. In one embodiment. R J O is CH 3 . CH 2 CH 3 , or cyclopropyl. In another embodiment of the compounds of formula 3. Rg is NR. S. C(=0)NR. NRC(=O). C(=0)0, OC(=O). OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR. NRC(=S)0. or NRC(=S)NR'. wherein R and R' are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and R 9 is hydrogen, OR" , SR", NR"R' ", alkyl. aryl. or heteroaryl. wherein R" and R'" are independently H, alkyl. aryl or heteroaryl. There further is provided compounds of formula 4: wherein: R7 is aryl or heteroaryl; R 8 is NR. S. C(=O)NR. NRC(=O). C(=O)O, OC(=O). OC(=O)NR. C(=S)NR. NRC(=S). OC(=S)NR, NRC(=S)0, or NRC(=S)NR' . wherein R and R' are independently H, alkyl, heteroalkyl, aryl or heteroaryl; and Rg is hydrogen. OR". SR". NR"R'", alkyl, aryl, or heteroaryl, wherein R" and R'" each are independently H. alkyl. heteralkyl. aryl or heteroaryl; and Rio and Ru are independently hydrogen, alkyl, heteroalkyl, aryl or heteroaryl, or NR 10 Rι 1 is NH 2 , NHC 1 - 4 alkyl, N(C,-C alkyl) 2 , or N(CH 2 ) 2 - There further are provided compounds of formula 5: wherein, in one embodiment: R 7 is aryl or heteroaryl; R 8 is NR. S. C(=0)NR. NRC(=O). C(=O)O. OC(=O). OC(=0)NR. C(=S)NR. NRC(=S), OC(=S)NR, NRC(=S)0. or NRC(=S)NR'. wherein R and R ' are independently H, alkyl, heteroalkyl. aryl or heteroaryl; and Rg is hydrogen. OR" . SR " . NR " R ' " . alkyl. aryl. or heteroaryl. w herein R " and R ' " each are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and Rio is alkyl. CpC. alkyl. heteroalkyl. aryl or heteroaryl. Also provided are compounds of formula 6: wherein in one embodiment: R 7 is aryl or heteroaryl; Rg is alkyl (such as C]-C 7 alkyl), alkenyl (such as Cj-C 7 alkenyl), alkynyl (such as C,-C 7 alkynyl), NR. O. S. C(=0)NR, NRC(=0), C(=0). C(=O)O. OC(=O), OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S), C(=S), C(=S)O. OC(=S), OC(=S)NR. NRC(=S)0, S(=O). SO : . S0 2 NR. NRSO : , NRCONR'. NRC(=S)NR' . or (CH 2 ) n O, wherein n = 0-20. such as 0-6. and wherein R and R ' are independently H. alkyl, heteroalkyl, aryl or heteroaryl ; R 9 is hydrogen. OH, OR", SR". NR"R' ". alkyl. aryl. heteroalkyl, or heteroaryl. and wherein R" and R' " are independently H, alkyl. heteroalkyl. aryl or heteroaryl: Rio and Ru are independently hydrogen, alkyl. heteroalkyl, aryl or heteroaryl: or NRioRn is NH : . NHC,- 4 alkyl. N(C,-C 4 alkyl)2. or N(CH 2 ) 2-5 . In one embodiment, there are provided compounds of formula 6. wherein: R 8 is NR. S. C(=O)NR. NRC(=0). C(=0)0. OC(=O). OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR. NRC(=S)0. or NRC(=S)NR ' . wherein R and R ' are independently H. alkyl. heteroalkyl. aryl or heteroaryl: and Rg is hydrogen. OR" . SR " . NR"R' ". alkyl. aryl. or heteroaryl. wherein R" and R ' " are independently H. alkyl. aryl or heteroaryl. Further provided are compounds of formula 7: wherein in one embodiment: R is aryl or heteroaryl: Rg is alkyl (such as Cj-C 7 alkyl). alkenyl (such as C 1 -C7 alkenyl). alkynyl (such as C 1 -C7 alkynyl). NR. O. S. C(=0)NR. NRC(=0). C(=O), C(=0)0. OC(=0). OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S). C(=S). C(=S)0. OC(=S). OC(=S)NR. NRC(=S)0. S(=O). S0 2 . S0 2 NR. NRS0 2 , NRCONR' , NRC(=S)NR'. or (CH 2 ) n O, wherein n = 0-6. and wherein R and R' are independently H. alkyl, heteroalkyl, aryl or heteroaryl; R 9 is hydrogen. OH. OR", SR", NR"R' ". alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R'" are independently H, alkyl, heteroalkyl. aryl or heteroaryl; and Rio is alkyl. heteroalkyl, aryl or heteroaryl. In one embodiment of the compounds of formula 7: Rg is NR. S. C(=O)NR. NRC(=O), C(=O)O, OC(=O). OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR. NRC(=S)0, or NRC(=S)NR', wherein R and R' are independently H. alkyl, heteroalkyl, aryl or heteroaryl; and Rg is hydrogen, OR" , SR", NR"R"\ alkyl, aryl, or heteroaryl, wherein R" and R ' " are independently H. alkyl. aryl or heteroaryl. Also provided are compounds of the structure lb: 1 b wherein, in one embodiment R 2 and R 4 are. independently, hydrogen, alkyl. heteroalkyl. heteroaryl or an electron withdrawing group, R 6 is thioacyl, aminocarbonyl, alkoxycarbonyl. aminothiocarbonyl, alkoxythiocarbonyl, alkylthιo(carbonyl), or alkylthιo(thιocarbonyl), and C(0)NR 7 Rg, C(S)NR 7 R 8 OC(0)NR 7 R 8 , OC(S)NR 7 R 8 , NR-C(0)N RgRg, NR 7 C(S)N R 8 R 9 , wherein R 7 . Rg, and R 9 are. independently, hydrogen, alkyl. heteroalkyl. aryl or heteroaryl. C(0)ORιo, wherein R J O is hydrogen, alkyl, heteroalkyl. aryl or heteroaryl, C(0)Rj j , wherein Ru is hydrogen, alkyl, heteroalkyl. aryl or heteroaryl, SR 12 , S(0) 2 Rj 2 . or S(0)Rj 2 , wherein Rj 2 is hydrogen, alkyl. heteroalkyl, aryl or heteroaryl, NRj 3 R| 4 wherein R 13 and Rj 4 are. independently, hydrogen, acyl. sulfonyl. alkyl. heteroalkyl, aryl or heteroaryl, 2-oxazolyl compπsing Rj 5 at the 4-posιtιon and R )6 at the 5- position of the oxazolyl, wherein Rj«; and Rι 6 are, independently, hydrogen, alkyl, heteroalkyl, aryl, heteroaryl or an electron withdrawing group, 2-ammothιazolyl compπsing R 17 at the 4-posιtιon and R] 8 at the 5- position of the thiazole, wherein R )7 and Rj 8 , are. independently. hydrogen, alkyl. heteroalkyl. aryl, heteroaryl or an electron withdrawing group, and CH 2 NRι R o- wherein R 19 and R 2 0 are. independently, hydrogen, alkyl. heteroalkyl. aryl. heteroaryl, acyl or sulfonyl. 2-( 1.3.4-thιadιazolyl) comprising R 1 at the 5-posιtιon of the 1.3.4- thiadiazole, wherein R 21 is hydrogen, alkyl. heteroalkyl, amιno(Cι_j alkyl). acylamιno(C|_ι alkyl), thιoacylamιno(C|_ 4 alkyl). sulfonamιdo(Cι_ 4 alkyl), heterocarbonylamιno(Cι. 4 alkyl). aryl. heteroaryl. an electron withdrawing group, or NR 2 2R 23 , wherein R 22 and R 2 7 are, independently, hydrogen, acyl, thioacyl, sulfonyl, alkyl, heteroalkyl. aryl or heteroaryl; CH=CHR 24 or C≡CR 24 . wherein R 24 is C(0)NR 7 Rg, C(S)NR 7 R 8 , OC(0)NR 7 Rg, OC(S)NR 7 R 8 , NR 7 C(0)N R 8 R 9 . NR 7 C(S)N R 8 R 9 , C(0)ORιo. C(0)R, j, SR,,, S(0) 2 Rj2. S(0)R 12 , NR, 3 R, , CH 3 NR, 9 R2o. alkyl, aryl. or heteroaryl: or 5.6-dιhydro-1.4.2-dιoxazιne-3-yl, wherein R 2 5 is at the 5-posιtιon of dioxazine, and R 26 is at the 6-posιtιon of dioxazine. and wherein R 25 and R 2& . are. independently, hydrogen, alkyl. heteroalkyl, aryl. heteroaryl or an electron withdrawing group; and wherein optionally Rj and R 2 together are a quinolone heterocycle C(=0)C(COOH)=CHNR 27 , or R] and R 2 together are a benzotπazole heterocycle NNNR 2 7. or NN(R 2 7)N. wherein R 27 is alkyl, aryl. or heteroaryl. Exemplary structures are shown below: In one embodiment of the compounds of formula lb Rj is C(0)NR 7 Rg. SR, ,. C(S)NR7R 8 . C(O)OR, 0 . C(0)R, ,. SR, : S(OM* 12 , S(0)R, : or NR n R, 4 In another embodiment of the compounds of formula lb Rj is NR (C=0)R \ . wherein R and R are independently hydrogen, alkyl. heteroalkyl, aryl. or heteroaryl In another embodiment. Rj is NR (Sθ 2 )R v . wherein R and R v are independently hydrogen, alkyl. heteroalkyl. aryl. or heteroaryl with the proviso that R v is not H In another embodiment. Rj is 2-oxazolyl, wherein Rj<; is at the 4- position and Rj 6 is at the 5-posιtιon of the oxazole group In a further embodiment, R| is 2-ammothιazolyl. wherein R| 7 is at the 4-posιtιon and Rjg is at the 5-posιtιon of the aminothiazolyl group In one embodiment of the compounds of formula lb. R 4 is hydrogen. R is fluoπne, R 6 is C(S)C, 7 alkyl or C(S)C 3 6 cycloalkyl, R, is C(0)NR 7 R 8 and R 7 is hydrogen, and/or R 8 is heteroaryl In another embodiment. R 4 is hydrogen. R is fluoπne. and/or R 6 is C(S)CH^, and NR 7 Rg is NH(5 ' -(5-amιnopyπdιne-2- yl)thιopyπdιne-3'-yl) or NH(pyπdιne-3-yl) or NH(5-chloropyπdme-3-yl) Exemplary compounds of formula 1 are as follows MIC refers to the minimal inhibitory concentration which was determined as descπbed in Example 37 In one embodiment, the compound shown below is provided, with, for example, an MIC of 4-8 Tg/mL (S aureus) In another embodiment, the five compounds shown below are provided, with, for example, an MIC of 0 25 to 4 Tg/mL (S. aureus). Other exemplary compounds include: Exemplary compounds active against a fastidious Gram-negative microorganism H. influenzae are the following five compounds with an MIC of 2-8 Tg mL (H. influenzae) : Also provided are compounds of formula 3c: 3c wherein in one embodiment: R 2 and R 4 are. independently, hydrogen, alkyl. heteroalkyl. heteroaryl or an electron withdrawing group; R ύ is thioacyl, aminocarbonyl, alkoxycarbonyl, aminothiocarbom l. alkoxythiocarbonyl. alkylthιo(carbonyl), or alkylthιo(thιocarbonyl), R 8 is alkyl (such as Cj-C 7 alkyl), alkenyl (such as C \ -d alkenyl). alkynyl (such as C,-C 7 alkynyl), NR. O. S. C(=0)NR. C(=S)NR. NRC(=0). NRC(=S). C(=O), C(=0)O. C(=S)O, OC(=0), OC(=S). S(=O), S0 2 , SO : NR. NRSO2, NRCONR" . NRCSNR'. or (CH 2 ) n O, wherein n = 0-20. such as 0-6. and wherein R and R ' are independently H, alkyl. heteroalkyl, aryl or heteroaryl; and Rg is hydrogen. OH, OR". SR". NR"R' ". alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R'" are independently H. alkyl. heteroalkyl. aryl or heteroaryl. In one embodiment of the compounds of formula 3c: R 6 is C(S)Ci.7 alkyl or C(S)C 3-6 cycloalkyl; R7 is aryl; R 8 ιs S: and R 9 is alkyl or heteroalkyl. In another embodiment of the compounds of formula 3c: R 6 is C(S)Ci. 7 alkyl or C(S)C 3 - 6 cycloalkyl, Ri is aryl; Rg is alkyl. In another embodiment of the compounds of formula 3c: R 6 is C(S)C| 7 alkyl or C(S)Cι. 6 cycloalkyl R7 is aryl. Rg is alkyl. Examples of compounds of formula 3c include the following compound with MIC-8 Tg/mL (S. aureus). Examples of compounds also include the following five compounds with IC 0.25-4 Tg/mL (S. aureus). Also provided are compounds of formula 4c 4c wherein in one embodiment: R 6 is thioacyl. aminocarbonyl, alkoxycarbonyl. aminothiocarbonyl. alkoxythiocarbonyl, alkylthιo(carbonyl), or alkylthιo(thιocarbonyl); Het, is heteroaryl. R 8 is alkyl (such as Cj-C 7 alkyl). alkenyl (such as Cj -C 7 alkenyl). alkynyl (such as Ci-Ci alkynyl). NR. O. S, C(=0)NR. C(=S)NR. NRC(=O). NRC(=S). C(=O). C(=O)O. C(=S)O. OC(=0). OC(=S). S(=0). S0 2 . SO 2 NR. NRSO;. NRCONR ' . NRCSNR'. or (CH : ) n O. wherein n = 0-20. e.g.. 0-6. and wherein R and R' are independently H. alkyl, heteroalkyl. aryl or heteroaryl; and R 9 is hydrogen. OH. OR". SR" . NR"R'". alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R'" are independently H. alkyl. heteroalkyl. aryl or heteroaryl Also provided are compounds of formula 5c: 5c wherein: R 2 and R4 are. independently, hydrogen, alkyl. heteroalkyl. heteroaryl or an electron withdrawing group: Re is thioacyl. aminocarbonyl. alkoxycarbonyl. aminothiocarbonyl. alkoxythiocarbonyl. alkylthιo(carbonyl). or alkylthιo( thiocarbonyl). Rg is alkyl (such as C,-C 7 alkyl), alkenyl (such as C1 . -C7 alkenyl). alkynyl (such as C 1 -C7 alkynyl). NR. O. S. C(=0)NR. C(=S)NR. NRC(=O). NRC(=S). C(=0), C(=O)O. C(=S)0. OC(=O). OC(=S). S(=O). S0 2 . S0 2 NR. NRSO ; . NRCONR " . NRCSNR' . or (CH 2 ) n O, wherein n = 0-20. e.g.. 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl. aryl or heteroaryl. and Het 2 is a heterocychc group. In one embodiment of the compounds of formula 5c: R 6 is C(S)Cj_7 alkyl or C(S)Cv6 cycloalkyl; R7 is aryl; Rg is S; and Het is a thienylphenyl or thiazolyl group. In another embodiment of the compounds of formula 5c: Rd is C(S)Cι-7 alkyl or C(S)Cv6 cycloalkyl, R 7 is aryl; R 8 ιs NH; and Het 2 is 1.3.5-tπazιnyl. In one embodiment, the compound has the structure. Other Oxazohdinone Compounds In another embodiment, there are provided compounds of formula 8. wherein: R 7 is aryl or heteroaryl. R 8 is C, -C- alkyl. C,-C 7 alkenyl. C,-C 7 alkynyl. NR. O. S. C(=0)NR. NRC(=0). C(=0). C(=0)0. OC(=0). OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S). C(=S). C(=S)0. OC(=S), OC(=S)NR. NRC(=S)0. S(=0). S0 . SO 2 NR. NRSO : . NRCONR'. NRC(=S)NR' . or (CH 2 ) n O, wherein n = 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl, aryl or heteroaryl; R 9 is hydrogen, OH. OR", SR", NR"R'". alkyl. aryl, heteroalkyl. or heteroaryl, and wherein R" and R'" are independently H. alkyl. heteroalkyl, aryl or heteroaryl. Rio and Ru are independently hydrogen, alkyl. heteroalkyl. aryl, heteroaryl. acyl. thioacyl. CN. NO 2 . alkoxycarbonyl. COOC 1 - 4 alkyl, sulfonyl. aminocarbonyl. aminothiocarbonyl. or alkoxythiocarbonyl; and R 12 is hydrogen, alkyl, heteroalkyl, aryl, or heteroaryl. Also provided are compounds of formula 9- O R <r-R s-R 7— N ^ I ^ ^ ^ \^>^ H S(O)n R 1 0 9 wherein: R 7 is aryl or heteroaryl; R 8 is C 1 -C7 alkyl. C,-C 7 alkenyl. C,-C 7 alkynyl. NR. O. S. C(=0)NR. NRC(=0). C(=0). C(=0)0, OC(=0), OC(=0)NR. NRC(=0)0, C(=S)NR. NRC(=S), C(=S), C(=S)0. OC(=S), OC(=S)NR, NRC(=S)0, S(=0). SO : . SO 2 NR. NRS0 2 . NRCONR'. NRC(=S)NR', or (CH 2 ) n O. wherein n = 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl. aryl or heteroaryl; Rg is hydrogen. OH, OR". SR", NR"R"\ alkyl. aryl, heteroalkyl. or heteroaryl, and wherein R" and R'" are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and Rio is alkyl. heteroalkyl. aryl, or heteroaryl. and n = 0-2. Further provided are compounds of formula 11: wherein: R 7 is aryl or heteroaryl; R 8 is C 1 -C7 alkyl. C,-C 7 alkenyl, C,-C 7 alkynyl, NR. O. S. C(=0)NR. NRC(=0), C(=0), C(=0)0. OC(=0), OC(=0)NR. NRC(=0)0. C(=S)NR, NRC(=S). C(=S), C(=S)0, OC(=S). OC(=S)NR. NRC(=S)0, S(=0), S0 2 , SO 2 NR. NRSO 2 , NRCONR'. NRC(=S)NR'. or (CH 2 ) n O. wherein n = 0-6. and wherein R and R' are independently H. alkyl, heteroalkyl, aryl or heteroaryl; Rg is hydrogen. OH. OR". SR". NR"R"\ alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R'" are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and Rio is alkyl, C 1 -4 alkyl, heteroalkyl, aryl or heteroaryl. In another embodiment, there are provided compounds of formula 12: wherein: R7 is aryl or heteroaryl; R g is C 1 -C7 alkyl. C 1 -C7 alkenyl, C,-C 7 alkynyl, NR. O. S. C(=0)NR. NRC(=0). C(=0), C(=0)0, OC(=0). OC(=0)NR, NRC(=0)0, C(=S)NR. NRC(=S). C(=S), C(=S)0. OC(=S), OC(=S)NR. NRC(=S)0, S(=0), S0 2 . S0 2 NR. NRSO 2 . NRCONR', NRC(=S)NR'. or (CH 2 ) π O. wherein n = 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl, aryl or heteroaryl; R Q is hydrogen. OH. OR". SR". NR"R"\ alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R" and R' " are independently H. alkyl, heteroalkyl. aryl or heteroaryl. Rm is alkyl. heteroalkyl. arvl or heteroaryl. and X = 0. S Further provided are compounds of formula 13 w herein R- is aryl or heteroaryl. Rg is C1-C7 alkyl. C,-C- alkenyl. C,-C 7 alkynyl. NR. O, S, C(=O)NR, NRC(=0). C(=0). C(=O)O. OC(=0), OC(=0)NR. NRC(=0)0. C(=S)NR. NRC(=S). C(=S). C(=S)0. OC(=S), OC(=S)NR. NRC(=S)0. S(=O). SO : . S0 2 NR. NRS0 2 . NRCONR'. NRC(=S)NR', or (CH 2 ) n O. wherein n = 0-6. and wherein R and R' are independently H, alkyl, heteroalkyl. aryl or heteroaryl, Rg is hydrogen. OH. OR". SR", NR"R' ". alkyl. aryl. heteroalkyl. or heteroaryl, and wherein R" and R'" are independently H. alkyl. heteroalkyl. aryl or heteroaryl, and R J O IS hydrogen, thiol. alkyl. heteroalkyl. aryl or heteroaryl Synthesis of Oxazolidmones Oxazolidmones such as 3-(heteroaryl)oxazohdιnones may be synthesized by a vaπety of routes as disclosed herein Exemplary methods of synthesis of oxazohdmone compounds are described in U S. Patent Application Seπal No 09/012,535. filed January 23, 1998. U S. Patent Application Serial No 09/086.702. filed May 28. 1998. U S Patent Application Seπal No 09/235.771, filed January 22. 1999. and PCT US99/01318. filed January 22. 1999. the disclosures of which are incorporated herein by reference their entirety In one embodiment, oxazohdmone compounds can be synthesized by attaching a plurality ot aryl or heteroaryl oxazolidmones to a plurality of solid supports, functiona zing the substituents aryl or heteroaryl groups of the attached oxazolidmones. removing the oxazolidmones from the solid supports in form of 5-amιnomethyloxazohdιnones; and functiona zing the amino group of cleaved 5-amιnomethyloxazohdιnones with an appropπate thioacylaung reagent(s) to produce 5-(thιocarbonyl )amιnooxazohdιnone derivatives The final thioacylation step can be performed, e g , with alkyl dithiocarboxylate The final thioacylation step can be performed, for example, with a polymeric reagent of the structure wherein R is an alkyl. aryl. heteroaryl, alkoxy, alkylthio, or amino group X is O. S. N-(alkoxy)amιne. benzotπazole. benzimidazolone. lmidazole. or alike electron withdrawing N-heterocychc group, and the polymer carrier is polystyrene, polyethyleneglycol (PEG). PEG grafted polystyrene, or alike polymer. The polymeric thioacylaung reagent can be produced by thioacylation of an alcohol, thiol. or NH-functionahzed polymer carrier. The polymeric thioacylaung reagent can be produced by stepwise reaction involving (l) acylation of NH-functionahzed polymer, and (n) conversion of the amide intermediate into reactive thioamide with thionation reagents, such as Lawesson, Davy. Yokoyama, or Belleau reagents. Na 2 P4Sn, Na 2 P SιoO. or alike known compounds capable of converting amides into thioamides. The polymeπc thioacylaung reagent can be produced by reaction of dithiocarboxylates with appropπate polymeπc alkylation reagents, such as chloroalkyl functionalized resins. In another embodiment, a method of prepaπng an oxazohdmone compound is provided, the method compπsing: attaching an aryl or heteroaryl oxazohdmone to a solid support to form a linkage between a functional group on the support and the nitrogen of a 5-amιnomethyl group of the oxazohdmone. acvlating the 5-amιnomethyloxazolιdιnone group of the attached oxazohdmone to form a 5-amιdomethyl group; functionahzing a substituent in an aryl or heteroaryl group of the attached oxazohdmone, converting the 5-amιdomethγl group of an attached oxazohdmone into a 5-thιoamιdo group, and removing the 5- thioamidomethyloxjzohdinone from the polymer carrier In another embodiment, a method for a solid phase synthesis of oxazohdmone compounds is provided comprising the treatment of an amide precursor compπsing a group such as NC(0)Rjo. immobilized on a support, wherein R J O is a substituent such as alkyl. heteroalkyl. aryl or heteroaryl, with a thionation reagent, and release of a compound of formula 3 from the support One embodiment is illustrated in Scheme 2 below Synthetic Schemes Embodiments of schemes for synthesis of oxazohdmone compounds are shown below by way of example Based on the disclosure herein a wide vaπety of oxazolidmones as defined herein may be synthesized The specific structures, such as the fluorophenyl ring, are shown by way of example, and are not to be considered to be limiting The synthesis may be readily conducted with other starting mateπals. including compounds compπsing other substituted or unsubstituted phenyl rings As illustrated in Scheme 1, below, for example. N-substituted 5-(S)- aminomethyloxazohdinones can be produced by transformations of 5-(S)- aminomethyloxazohdinones with vaπous known electrophihc reagents capable of reacting with a pπmary or secondary amines with or without use of organic or inorganic bases In one embodiment, such syntheses can be performed in solution using 5- (S)-amιnomethyloxazohdιnone deπvatives as pπmary amine reagents In another embodiment. 5-(S)-amιnomethyloxazohdιnone or 5-(S)- azidomethyloxazohdinones can be first immobilized on polymeπc supports using appropπate linker groups (e g . aldehyde or benzyl halide - type acid- or photo- cleavable linkers) to produce an immobilized 5-(S)-amιnomethyloxazolιdιnone The latter functionalized compounds can be treated with appropπate electrophihc reagents to introduce the desired N-substιtuent(s) Resulting tethered products can be released from supports using cleavage reagents (e g , tπfluororacetic acid) or light (when photocleavable linkers are employed) Solution syntheses trom 5-(S)-amιnomethvloxazolιdιnone denvatives: 2. Solid phase syntheses trom immobilized 5-(S)-amιnomethyloxazohdιnone deπvatives: R 2 = For example. RC(=S). ROC(=S), RNR'C(=S). RSC(=S). RS(=0). (RO) 2 P(=0). (RO) 2 P(=S). where R. Rj and R' are substituents such as alkyl or heteroalkyl. X = CI, Br, SR. OR, S0 2 R. benzotπazole, or other electron withdrawing leaving group. Scheme 1. Examples tor general syntheses of N-substituted 5-(S)-amιnomethyloxazolιdιnone deπvatives. The synthesis is shown generally below in Scheme la. 1 Synthesis trom 5-(S)-amιnomethvl deπvatives and electrophihc capping reagents R = For example. RC(=S), ROC(=S). RNR'C(=S), RSC(=S), RS(=0). (RO) 2 P(=0), (RO) 2 P(=S), X = CI, Br, SR, OR, S0 2 R, benzotnazole. or other electron withdrawing leaving group Examples: RX = RC(=S)SAlk. ROC(=S)Cl. RSC(=S)SAlkl, RS(=0)C1. (R0) 2 P(=0)C1.(R0) 2 P(=S)C1, All Ri 5 , R, and R' groups are independently different substituents such as alkyl and heteroalkyl Synthesis from 5-(S)-amιdomethyl deπvaϋves and thionation reagents Thionation reagent = Lawesson, Davy, Yokoyama, or Belleau reagents. P4S 10 , Na 2 P 4 Sj j .or Na 2 P SjoO, or other reagent capable of convening the amide group into thioamide group. Rι, R 2 , R , and R are independently selected substituents Scheme la. Examples for general synthesis of N-substituted 5-(S)-amιnomethyloxazohdιnone deπvauves In another embodiment, the resulting tethered N-substituted 5-(S)- aminomethyloxazohdinone deπvatives can be subjected to vaπous chemical transformations in other parts of the molecule pπor to the cleavage from supports, analogously to such transformations of immobilized 5-(S)- amidomethyloxazohdinones as descπbed m U S Patent application Seπal No 09/235.771 (PCT/US99/0138) Embodiments for the synthesis of 5(S)thioamidomethyloxazolidinone derivatives are shown below in Scheme 2. 1. Synthesis from 5-(S)-aminomethyl derivatives and dithiocarboxylates: 2. Synthesis from 5-(S)-amidomethyl derivatives and Lawesson reagent: o S 3. Synthesis from 5-(S)-amidomethyl derivatives and thionation reagents: Thionation reagent = Lawesson, Davy, Yokoyama, or Belleau reagents, P 4 S 1 Q, Na 2 P Sι. j, or Na 2 P 4 S 10 O, or other reagent capable of converting the amide group into thioamide group, and R] and R 2 are independently substituents such as alkyl and heteroalkyl. Scheme 2. General syntheses of 5-(S)-thioamidomethyloxazolidinone derivatives. Exemplary synthetic routes are also shown generally below in Scheme 2a. 1 Synthesis trom 5-(S)-amιnomethyl deπvatives and dithiocarboxylates 2 Synthesis from 5-(S)-amιdomethyl deπvatives and Lawesson reagent 3 Synthesis from 5-(S)-amιdomethyl deπvatives and thionation reagents Thionation reagent = Lawesson, Davy, Yokoyama, or Belleau reagents, P 4 S|r Na 2 P S[ [, or Na 2 P 4 SιoO, or alike reagent capable of converting the amide group into thioamide group. Rι_ 6 , and R' are independently selected substituents such as alkyl or heteroalkyl Scheme 2a. General syntheses of 5-(S)-thιoamιdomethyloxazohdιnone deπvauves. In one embodiment, 5-(S)-thιoamιdomethyloxazohdιnone deπvatives can be produced in solution by transformation of 5-(S)-amιnomethyloxazohdιnones with vaπous electrophihc reagents capable of thioacylation of the pπmary amine groups In another embodiment, 5-(S)-amιnomethyloxazohdιnones can be first acylated to produce 5-(S)-amιdomethyloxazohdιnones intermediates. The latter then can be converted into desired thioamides using vaπous thionation reagents, such as Lawesson. Davy. Yokayama or Belleau reagents For a decπption of Lawesson reagents. se M P Cava. M I Levmson. Tetrahedron ( 1985). 41 5061 For a description of Davy reagents, see H Davy. Chem Commun , ( 1982) p 457 For a description of Yokoyama reagents, see M Yokoyama et al . Svtithests. ( 1984) p 827 For a description of Belleau reagents, see Tetrahedron Lett . 1983. 24, p 3815 For a decπption of Heimgartner reagents, see P Wipf. C Jenny, and H Heimgartner Helv Chim Acta. (1987) 70, p 1001 For a description of P4S 1 0 and related reagents, see E Campaigne, The Chemistry of the Carbotrvl Group (Ed S Patai), Chap 17 Interscience. New York, 1966 For a description of Na 2 P 4 Su reagents, see D. Bπllon , Svnth Commun.. ( 1992) 22. p 1397 For a description of Na P4SjoO reagents, see D Bπllon, Synth Commun , ( 1990). 20. p 3085 The disclosure of these and all other publications referred to herein are incorporated herein by reference in their entirety In another embodiment, the thionation step can be performed on immobilized 5-(S)-amιdomethyloxazohdιnones Resulting products can be released from supports using chemical cleavage reagents (such as TFA for acid- cleavable resins) or light (when photocleavable linker res is employed) Another illustrative example of a general synthetic scheme for the synthesis of substituted amιnomethyl-3-aryloxazolιdιnone compounds is shown below in scheme 3a. MeONa MeOH Rl arτl R2 are lr ieperrterfy s±sαtjjertB such a^ Scheme 3a Examples for general syntheses of substituted 5-(S)-amιnomethyl-3-arvloxazohdιnone deπvatives In another embodiment, either tethered 5-(S)- thioamidomethyloxjzohdinone derivatives or their 5-(S)-amιdomethyl- oxazohdinone precursors can be subjected to various chemical transformations on solid supports prior to the cleavage or transformation into thioamides analogously to such reactions of immobilized 5-(S)-amιdomethyloxazohdιnones described in U.S. Patent Application Serial No. 09/235.771 ). In another example, oxazohdmone compounds are synthesized in part on a solid support as shown below in scheme 3 R 2 = a substituent such as alkyl. aryl. heteratom. NHR. OR. SR; X = SR'. OR'. CI. benzotπazole. lmidazole. or other leaving group, where Rj, R 2 . R. and R' are independently substituents such as alkyl or heteroalkyl. Scheme 3. A general synthesis ot an array of 5-(thιocarbonyl)amιnooxazohdιnιnes involving (I) immobilization of amine reagents on polymeric supports, (n) funcnonalizations in position 4 of the aromatic group, (in) cleavage of 5-amιnomethyl- oxazolidmones from resin, and (iv) i n functionalization with appropπate thioacylating reagent(s). 5-(S)-amιnomethyloxazohdmone deπvatives can be immobilized on polymeπc supports to produce reactive tethered intermediates The latter can be further modified in various part of the molecule using functional group 15 transformations to derive the desired structures. These can be cleaved from a support in form of the novel 5-(S)-amιnomethyloxazohdιnone structures that can be converted into thioamides using various thioacylating reagents as descπbed for a solution synthesis of such compounds In another embodiment, oxazohdmone compounds can be synthesized as shown below in Scheme 4 B Support is Sasπn resin or TEA Scheme 4. An example of oxazohdmone thioamide synthesis involving (l) immobilization ot amine oxazohdmone reagent on solid supports, (n) cleavage of the 5-amιnomethyloxazolιdιnone intermediate from resin, and (in) thioacylation to provide 5-thιoamιdomethyloxazolιdιnone For example, 5-(S)-amιnomethyloxazolιdιnone deπvatives can be reacted with Wang or Sasπn lmidazole carbamate resins to produce oxazolidmones immobilized via acid cleavable carbamate linkage. 5-(S)- Aminomethyloxazohdinone can be released from such supports by TFA treatment and further converted into thioamide deπvatives via thioacylation with alkyl dithiocarboxylate reagents in solution Scheme 5 below shows an example of the synthesis of an oxazohdmone thioamide using a polymeπc thioacylating agent 907c TFA/DCM A Support is Wang resin B Support is Sasπn resin X = O Polymer is deπvatized Argogel. Ar oWang, or HOBt polystyrene resin (for preparation, see Scheme 7), X = S Polymer is deπvatized polystyrene or PEG grafted polystyrene ( for preparation, see Scheme 8 ) Scheme 5. An example ot oxazohdmone thioamide synthesis involving cleavage ot the 5-amιnomethyloxazolιdιnone intermediate from resin and thioacylation with a polymeπc thioacylating reagent to provide 5-thιoamιdomethyloxazolιdιnone Transformation of 5-(S)-amιnomethyloxazohdιnones into thioamides can be effected using polymeπc thioacylating reagents to provide an advantage of 5 easy products separation. In one embodiment, this can be performed using dithiocarboxylate resin deπvatives. In one embodiment, polymeπc thioacylating reagents can be produced by thioacylation of suitable OH. SH, or NH-functionahzed supports with reagents capable of this transformation in solution phase, as shown below in Scheme 6. R V Y Hx-o ( —Base an -d —or H ►eat) R Y S X" 0 X = O. S. heterocychc NH group. (RO)NR' group, or other functionality. Polymer is polystyrene, polyethyleneglycol (PEG). PEG grafted polystyrene, or alike resin. R = Substituents such as alkyl. aryl. heteroalkyl. NHR'. OR'. SR'; and R' is a substituent. Y = CI. SR. OR. lmidazole. benzotπazole. nitrobenzotπazole. benzimidazolone. (fluoro or nitro (benzimidazolone. or alike leaving group. Scheme 6. Examples for general syntheses of the polymeπc thioacylating reagents via i n thioacylation of appropπate OH. SH. or NH-deπvatized polymers. In another embodiment, polymeric thioacylating reagents can be produced by alkylation of dithiocarboxylate salts with a polymeπc support compπsing reactive alkylation functionalities, such as benzyl or alkyl chloride groups, as shown below in Scheme 7 M = MgHal. Na. Li. Y = CI. Br. TsO. or other leaving group or other metal group Polymer is polystyrene, polyethyleneglycol (PEG). PEG grafted polystyrene, or alike resin. R is a substituent such as alkyl Scheme 7. Examples for general syntheses of the polymeπc thioacylating reagents via reaction ot dithiocarboxylates with polymer alkylating agents. Scheme 8 below shows the general synthesis of polymeric thioacylating agents. NHR' = heterocyclic NH group, such as imidazole. benzotπazole. nitrobenzotπazole. benzιmιdazolone,(fluoro or nιtro)benzιmιdazolone; (RO)NR' group; or other acidic NH functionality. Polymer is polystyrene, polyethyleneglycol (PEG), PEG grafted polystyrene, or alike resin. R = is a substituent such as alkyl. aryl. heteroatom. or heteroalkyl X = CI. SR, OR. or other leaving group. Scheme 8. Examples for general syntheses of the polymeπc thioacylating reagents via thionation of appropπate acylated NH-functionahzed polymers Thioacylating polymeπc reagents can be produced by transformation of suitable immobilized amides into thioamides using thionation reagents, such as Lawesson. Davy. Yokoyama. or Belleau reagents, phosphorus pentasulfide and other chemicals capable of the transformation Resulting thioamides comprising a thiocarbonyl group attached to an electron withdrawing nitrogen atom can be used to thioacylate the primary amine group of 5-(S )-amιnomethyloxazolιdιnone derivatives. An example of the use ot polymeric thioacylating reagents in the preparation of oxazolidmones is shown below in Scheme 9. Scheme 9. Examples for syntheses of polymeric thioacylating reagents used in preparation of 5-thιoamιdomethyloxazohdιnones. Polymeπc thioacylating reagents can be produced by thioacylation of an alcohol group functionalized polymers. Resulting thionoester resin can be used to effect the conversion of 5-(S)-amιnomethyloxazohdιnones into reactive thioamide deπvatives. Examples of the use of polymeπc thioacylating agents for the preparation of oxazolidmones is shown below in Scheme 10. C1 v_ M e - M2 χ ^ Me Y SM " X — → Me γ S - } s s PEG grafted Memfield resin polystyrene Scheme 10. Examples for preparation of polymeπc thioacylating reagents used for preparation of 5-thιoamιdomethyloxazolιdιnones The thioacylating reagent can be made from Gπgnard reagents, carbon disulfide. and chloroalkyl functionalized polymer, such as polyethyleneglycol grafted polystyrene, cross-linked divinylbenzene- polystyrene, and other similar polymeric mateπals As shown in Scheme 1 1 below, in another embodiment. 5-(S)- aminomethyloxazolidinone deπvatives can be immobilized on a polymeπc support(s) with a suitable linker functionality (such as aldehyde or benzyl chloride type group) and then acylated to produce immobilized 5-(S)- amidomethyloxazohdinone deπvatives These tethered amide intermediates can be converted into thioamides on a solid phase using thionation reagents capable of transformation of a secondary amine group into thioamide functionality Resulting products can be released from the support using chemical or photo- cleavage depending on the nature of the linker group. Thionation Resin is a cleavable polymer Cleavage Thionation reagent = Lawesson, Davy, Yokoyama. or Belleau reagents, P 4 S I 0 , j , or Na-ιP S ] oO. or other reagent capable of converting the amide group into thioamide functionality R and R' are substituents such as alkyl. aryl, heteroalkyl Scheme 11. Example for a general synthesis of 5-thιoamιdomethyloxazohdιnone synthesis involving a thionation of oxazolidinone amide derivative attached to a polymeric carrier For example, as shown below in Scheme 12. BAL linker immobilized 5- (S)-amιdomethyl-3-[4 ' -mo hohno-3 ' -fluoro]phenyloxazohdme-2-one was converted into respective thioamide using Lawesson reagent in dioxane The resulting product was released from the support using TFA cleavage Scheme 12. An example for 5-thιoamιdomethyloxazolιdιnone synthesis involving a thionation of oxazohdmone amide derivative attached to a polymeπc carrier As will be appreciated by those skilled in the art. using these and other methods disclosed herein, based on the teachings of the specification, the oxazolidinones disclosed herein can be readily synthesized. Solid Supports The solid phase synthesis of the compositions provided herein in one embodiment is performed on a solid support. "Solid support" includes an insoluble substrate that has been appropriately derivatized such that a chemical module can be attached to the surface of the substrate through standard chemical methods. Solid supports include, but are not limited to, beads and particles such as peptide synthesis resins. For example, see Merrifield ( 1963) J. Am. Chem. Soc. 85:2149-2154; U.S. Patent No. 4.631.211; and Geysen et al. (1984) Proc. Natl. Acad. Sci. USA 81 :3998-4002. Solid supports can consist of many mateπals, limited pπmarily by the capacity of the mateπal to be functionalized through synthetic methods. Examples of such mateπals include, but are not limited to. polymers, plastics. resins, polysacchaπdes. silicon or silica based mateπals. carbon, metals, inorganic glasses and membranes. Preferred resins include Sasr resin (a polystyrene resin available from Bachem Bioscience. Switzerland), Wang resin or p- mtrophenylcarbonate Wang resin (PNP resin. Novabiochem). and TentaGel S AC. TentaGel PHB. or TentaGel S NH 2 resin (polystyrene-polyethylene glycol copolymer resins available from Rapp Polymere. Tubingen. Germany or from Perseptive, Boston) The solid support can be purchased with suitable functionality already present such that a chemical module can be attached to the support surface (e.g . Novabiochem. Bachem Bioscience. Rapp Polymere) Alternatively, the solid support can be chemically modified such that a chemical module can be attached to the support surface. Grant (1992) Synthetic Peptides. A User's Guide, W.H. Freeman and Co.; and Hermkens et al. (1996) Tetrahedron 52.4527-4554 One of ordinary skill in the art will understand that the choice of functionality used for attaching a molecule to the solid support will depend on the nature of the compound to be synthesized and the type of solid support. Examples of functionality present on the solid support that can be used to attach a chemical module include, but are not limited to. alkyl or aryl hahdes, aldehydes, alcohols, carbonates, ketones, amines, sulfides, carboxyl groups, aldehyde groups and sulfonyl groups. The functional group on the solid support that permits the attachment of a chemical module is, for example, an alcohol, an amine. an aldehyde, a carbonate, or a diol group. Gordon et al. ( 1994) J. Med. Chem. 37: 1385-1401 ; and Hermkens et al. (1996) Tetrahedron 52:4527-4554. For making certain combinatoπal libraπes, one can purchase a solid support with an existing, protected chemical module already attached. An example of such a support is FmocGly Sasπn, which is commercially available from Bachem. Typically, however, the first step of the comb atonal library synthesis is the attachment of a chemical module to the solid support through the existing functionality on the support surface. Examples of chemical reactions that can be used to attach a chemical module to the support include, but are not limited to. nucleophihc displacement of a hahde or other leaving group, etheπfication of an alcohol, esteπfication of an alcohol, amidation of an amine, carbamation of an amme. reductive animation of a carbonyl compound, acetahzation of an aldehyde and ketahzation of a ketone. Hermkens et al. (1996) Tetrahedron 52:4527-4554. The reaction used to attach the chemical module to the solid support is, for example, a carbamation of an amine. a reductive animation of a carbonyl compound or a nucleophihc displacement ot a hahde or other leaving group For example, see Hermkens et al ( 1996) For the attachment of certain chemical modules to the solid support, it may be necessary to mask tunctionahty that is not involved in the attachment process. but that is incompatible with the mode of attachment A non-limiting example of this type of process is the esteπfication of an alcohol functionalized solid support, using a hydroxyl-substituted carboxylic acid as the coupling partner. Pπor to the esteπfication reaction, the hydroxyl group of the carboxylic acid would be "protected" through alkylation. silylation. acetylation. or through another method known to one of skill in the art. Strategies for the use of masking or protecting groups have been well-described in the art. such as in Green ( 1985) Protecting Groups in Organic Synthesis. Wiley. Methods of Compound Cleavage from a Solid Support The cleavage of oxazolidmones from a solid support to produce the corresponding "free" compounds can be accomplished using a vaπety of methods. For example, a compound can be photolytically cleaved from a solid support (Wang et al. ( 1976) J. Org. Chem. 41 :3258. Rich et al. (1975) J Am. Chem. Soc. 97 1575- 1579). and through nucleophihc attack (U.S. Patent No. 5.549.974), or through hydrolysis (Hutchins et al. (1994) Tetrahedron Lett. 35:4055-4058) The cleavage of compounds from a solid support to produce soluble compounds is accomplished, for example, using hydrolytic conditions, such as through the addition of tπfluoroacetic acid. Screening The oxazohdmone compounds can be screened to identify bioactive molecules with different biological activities using methods available in the art The bioactive molecules, for example, can possess activity against a cellular target, including but not limited to enzymes and receptors, or a microorganism. A target cellular hgand or microorganism is one that is known or believed to be of importance in the etiology or progression of a disease. Examples of disease states for which compounds can be screened for biological activity include, but are not limited to. inflammation, infection, hypertension, central nervous system disorders, and cardiovascular disorders In one embodiment of screening, for example, an enzyme solution can be mixed with a solution of the compound(s) under conditions favorable to enzyme- hgand binding See Bush et al ( 1993) Antimicrobial Agents and Chemotherapy 37 851-858. and Daub et al ( 1989) Biochemistry 27 3701-3708 Specific binding of compounds to the enzyme can be detected, for instance, by any of the numerous enzyme inhibition assays which are well known in the art Compounds which are bound to the enzyme are separated readily from compounds which remain free in solution by applying the solution to a suitable separation mateπal such as Sephadex G-25 gel filtration column Free enzyme and enzyme-hgand complexes pass through the column quickly, while free compounds are retarded in their progress through the column The mixture of enzyme-hgand complex and free enzyme is then treated with a suitable denaturing agent, such as guanidi um hydrochloπde or urea, to cause release of the hgand from the enzyme The solution is then injected onto an HPLC column (for example, a Vydac C-4 reverse-phase column, and eluted with a gradient of water and acetomtπle ranging from 0% acetonitπle to 80% aceto tπle). Diode array detection provides discnmination of the compounds of the combinatoπal library from the enzyme. The compound peaks are then collected and subjected to mass spectrometry for identification Finding a compound that inhibits an enzyme is performed most readily with free compound in solution. The compounds can also be screened while still bound to a resin used for synthesis; in some applications, this may be the preferable mode of finding compounds with the desired characteπstics. For example, if a compound that binds to a specific antibody is desired, the resin- bound library of compounds is contacted with an antibody solution under conditions favoπng a stable antibody-compound-resin complex A fluorescently labeled second antibody that binds to the constant region of the first antibody is then contacted with the antibody-compound-resin complex This allows identification of a specific bead as carrying the compound recognized by the first antibody binding site The bead is then physically removed from the resm mixture and subjected to mass spectral analysis. If the synthesis is conducted in a manner such that only one compound is likely to be synthesized on a particular bead, then the binding compound has been identified . If the synthesis is carried out so that many compounds are present on a single bead, the information derived from analysis can be utilized to naπow the synthetic choices for the next round of synthesis and identification The enzyme, antibody, or receptor target need not be in solution Antibody or enzyme can be immobilized on a column The compound(s) is then passed over the column, resulting in the retention of strongly binding compounds on the column after weaker-binding and non-bmdmg compounds are washed away The column is then washed under conditions that dissociate protein-hgand binding, which removes the compounds retained in the initial step These compounds are then analyzed, and synthesized separately in quantity for further testing Similarly, cells beaπng surface receptors are contacted with a solution of compounds The cells beaπng bound compounds are readily separated from the solution containing non-binding compounds. The cells are then washed with a solution which dissociates the bound hgand from the cell surface receptor Again, the cells are separated from the solution, and the solution analyzed The compounds also may be assayed for β-lactamase inhibition using methods available in the art Pharmaceutical Compositions The present invention also provides pharmaceutical compositions which compπse a bioactive oxazohdmone compound or a salt such as a pharmaceutically acceptable salt thereof and optionally a pharmaceutically acceptable earner The compositions include those in a form adapted for oral, topical or parenteral use and can be used for the treatment of bacteπal infection in mammals including humans The compounds, such as antibiotic compounds, also referred to herein as antimicrobial compounds, according to the invention can be formulated for administration in any convenient way for use in human or veteπnary medicine, by analogy with other bioactive agents such as antibiotics Such methods are known in the art and are not described in detail herein The composition can be formulated for administration by any route known in the art. such as subdermal. by-inhalation, oral, topical or parenteral The compositions may be in any form known in the art. including but not limited to tablets, capsules, powders, granules, lozenges, creams or liquid preparations, such as oral or sterile parenteral solutions or suspensions The topical formulations of the present invention can be presented as. for instance, ointments, creams or lotions, eye ointments and eye or ear drops. impregnated dressings and aerosols, and may contain appropπate conventional additives such as preservatives, solvents to assist drug penetration and emollients in ointments and creams. The formulations may also contain compatible conventional carriers, such as cream or ointment bases and ethanol or oleyl alcohol for lotions. Such carriers may be present, for example, from about 1% up to about 98% of the formulation. For example, they may form up to about 80% of the formulation. Tablets and capsules for oral administration may be in unit dose presentation form, and may contain conventional excipients such as binding agents, for example syrup, acacia, gelatin, sorbitol, tragacanth, or polyvinylpyrolhdone; fillers, for example lactose, sugar, maize-starch, calcium phosphate, sorbitol or glycme; tabletting lubπcants, for example magnesium stearate. talc, polyethylene glycol or silica; dismtegrants. for example potato starch; or acceptable wetting agents such as sodium lauryl sulphate. The tablets may be coated according to methods will known m normal pharmaceutical practice. Oral liquid preparations may be in the form of, for example, aqueous or oily suspensions, solutions, emulsions, syrups or elixirs, or may be presented as a dry product for reconstitution with water or other suitable vehicle before use. Such liquid preparations may contain conventional additives, such as suspending agents, for example sorbitol. methyl cellulose, glucose syrup, gelatin, hydroxyethyl cellulose, carboxymethyl cellulose, aluminium stearate gel or hydrogenated edible fats, emulsifying agents, for example lecithin, sorbitan monooleate. or acacia, non-aqueous vehicles (which may include edible oils), for example almond oil. oily esters such as glyceπne. propylene glycol. or ethyl alcohol, preservatives, for example methyl or propyl p-hydroxybenzoate or sorbic acid. and. if desired, conventional flavoπng or coloring agents For parenteral administration, fluid unit dosage forms are prepared utilizing the compound and a steπle vehicle, water being preferred The compound, depending on the vehicle and concentration used, can be either suspended or dissolved in the vehicle or other suitable solvent In preparing solutions, the compound can be dissolved in water for injection and filter steπhzed before filling into a suitable vial or ampoule and sealing. Advantageously, agents such as a local anesthetic preservative and buffering agents can be dissolved in the vehicle. To enhance the stability, the composition can be frozen after filling into the vial and the water removed under vacuum The dry lyophilized powder is then sealed in the vial and an accompanying vial of water for injection may be supplied to reconstitute the liquid prior to use. Parenteral suspensions are prepared in substantially the same manner except that the compound is suspended in the vehicle instead of being dissolved and steπhzation cannot be accomplished by filtration. The compound can be steπhzed by exposure to ethylene oxide before suspending in the steπle vehicle. Advantageously, a surfactant or wetting agent is included in the composition to facilitate uniform distribution of the compound. The compositions may contain, for example, from about 0.1% by weight, e.g . from about 10-60% by weight, of the active mateπal, depending on the method of administration. Where the compositions compπse dosage units, each unit will contain, for example, from about 50-500 mg of the active ingredient The dosage as employed for adult human treatment will range, for example, from about 100 to 3000 mg per day, for instance 1500 mg per day depending on the route and frequency of administration. Such a dosage corresponds to about 1.5 to 50 mg/kg per day. Suitably the dosage is. for example, from about 5 to 20 mg/kg per day Pharmaceutical Applications The oxazolidmones disclosed herein can be used in a vaπety of pharmaceutical applications In one embodiment, the compounds may be used as antimicrobial agents for the treatment of infectious disorders that are caused by microbial agents, such as bacteπa. In one embodiment, compositions, for treating or preventing infectious disorders are provided, compπsing an oxazohdone compound as disclosed herein in combination with a pharmaceutically acceptable earner In another embodiment, there is provided a dosage amount of an oxazohdmone as disclosed herein in an effective amount for the treatment, prevention or alleviation of a disorder, such as an infectious disorder Oxazolidmones can be screened for activity against different microbial agents and appropriate dosages may be determined using methods available in the art The compounds may be used to treat a subject to treat, prevent, or reduce the seventy of an infection Subjects include animals, plants, blood products cultures and surfaces such as those of medical or research equipment, such as glass, needles and tubing In one embodiment, methods of treating or preventing an infectious disorder in a subject, such as a human or other animal subject, are provided, by admimstenng an effective amount of an oxazohdmone as disclosed herein to the subject In one embodiment, the compound is administered in a pharmaceutically acceptable form optionally in a pharmaceutically acceptable earner As used herein, an "infectious disorder" is any disorder charactenzed by the presence of a microbial infection, such as bacteπal infections Such infectious disorders include, for example central nervous system infections, external ear infections, infections of the middle ear. such as acute otitis media, infections of the cranial sinuses, eye infections, infections of the oral cavity, such as infections of the teeth, gums and mucosa, upper respiratory tract infections, lower respiratory tract infections, genitouπnary infections, gastrointestinal infections, gynecological infections, septicemia. bone and joint infections, skin and skin structure infections, bacteπal endocarditis, burns, antibacteπal prophylaxis of surgery, and antibactenal prophylaxis in immunosuppressed patients, such as patients receiving cancer chemotherapy, or organ transplant patients The compounds and compositions compπsing the compounds can be administered by routes such as topically, locally or systemically Systemic application includes any method of introducing the compound into the tissues of the body, e g . intrathecal, epidural. intramuscular, transdermal. intravenous, intraperitoneal. subcutaneous, sublingual. rectal, and oral administration. The specific dosage of antimicrobial to be administered, as well as the duration of treatment, may be adjusted as needed. The compounds of the invention may be used for the treatment or prevention of infectious disorders caused by a vaπety of bactenal organisms. Examples include Gram positive and Gram negative aerobic and anaerobic bacteria, including Staphylococci. for example S. aureus; Enterococci. for example E. faecalis; Streptococci, for example 5. pneumoniae; Haemophilus. for example H. influenza; Moraxella, for example M. catarrhalis; and Escherichia, for example E. coli. Other examples include Mycobactena, for example M. tuberculosis; intercellular microbes, for example Chlamydia and Rickettsiae; and Mycoplasma. for example M. pneumoniae. The following examples are provided to illustrate but not limit the claimed invention. EXAMPLES Abbreviations ACN, acetomtπle, CDI. carbonyldπmidazole, DEEA. diethyhsopropylamine, DCM. dichloromethane; DIC. dnsopropyldnmide: DMF. dimethylformamide; HATU, 0-(7-azabenzotnazol-l-yl)-l, l,3.3- bιs(tetramethylene)-uronιum hexafluorophosphate; NMM, N-methyl morpholine, wzCPBA. m-chloro-peroxybenzoic acid, TFA, tπfluoroacetic acid, THF, tetrahydrofuran; TMOF, tπmethylorthoformate; PTLC, preparative thin layer chromatography. General. Reagents were obtained from Aldπch (St. Louis, MO), Sigma (St. Louis. MO), Bachem Biosciences, Rapp Polymere. Perseptive, and Novabiochem. and used without further punfication. The resin Tentagel S NTi was purchased from Rapp Polymere. Concentration of solutions after workup was performed by reduced pressure rotary evaporation, or using the Savant's SpeedVac instrument. Reactions with moisture-sensitive reagents were performed under nitrogen atmosphere. Mass-spectra were obtained using ESI technique. HTLC analysis and punfication were performed using Beckman System Gold R ® ; detection at 220 nm. Analytical EPLC was performed on YMC 5 micron C18 (4.6 mm x 50 mm) reverse phase column (gradient from 100% of the aq. 0.1 % TFA to 100% of 0.1 % TFA in MECN over 6 mm', flow rate 2.0 mL/min). Preparative TLC was performed using EM silica gel 60 F 254 plates (20 x 20 cm, thickness 2 mm). NMR spectra were obtained on a Vaπan Gemini 300 MHz instrument with CDCh as solvent, unless otherwise noted. 1H NMR spectra were reported as follows: chemical shift relative to tetramethylsilane (0.00 ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, b = broad), coupling, and integration. Example 1 : General Methods for Preparation of 5-(S)- Thioamidomethyloxazolidinones. A Synthesis from 5-(S )-Amιnomethyloxazohdιnone Derivatives and Ethyl Dithioacetate A solution of an appropriate 5-(S)-amιnomethyloxazohdιnone deπvative ( 1.0 mmol) and ethyl dithioacetate (0.130 ml. 1.13 mmol) with tπethylamine (0 215 ml.1.54 mmol) in dichloromethane was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue purified by PTLC (MeOH - DCM mixtures) or crystallization from appropnate solvent. B Synthesis from 5-(S)-Amιdomethyloxazohdιnone Derivatives and Lawesson Reagent. A mixture of an appropπate 5-(S)-amιdomethyl-oxazohdιnone deπvative (0.3 mmol) and Lawesson's reagent (0.0654 g, 0.15 mmol) in dioxane (3 ml) was stirred and heated at 65 °C for 2 hours. The solution was concentrated under vacuum and the crude product punfied by PTLC. C Solid Phase Synthesis from Immobilized 5-(S)-Amιdomethyl- oxazohdinone Deπvatives. A mixture of an appropπate 5-(S)-amιdomethyloxazohdιnone immobilized derivative (such as descπbed in U.S. Pat. Application Ser. No. 09/235.771 and in PCT US99/01318) (0.1 mmol) and an appropπate thionation reagent (0.1 - 1.0 mmol) in dioxane or THF (2-10 mL) Lawesson's reagent (0.15 was stirred at 0-65 °C for 2-10 hours (preferably, at 0-25°C for P 4 Sj 0 , Na 2 P 4 Sι ι or Na : P 4 S, 0 O. and at 40-65 °C for Lawesson. Belleau. or Davy reagents). The resin was washed liberally with DMF. DCM. MeOH. and dπed under vacuum. The product was cleaved from support with 10% TFA DCM (2-4 mL. r t.. 2 h). solvents removed under v acuum, and the crude product punfied by PTLC. Example 2: Synthesis of Intermediates. 2-Fluoro-4-nιtrobenzoιc Acid Concentrated sulfuπc acid (32 ml) was added carefully with stirring to a solution of 2-fluoro-4-mtrotoluene ( 16 5 g. 0 106 mol) in acetic acid (200 ml ) The mixture was warmed up to 95 °C. and solution of chromium tπoxide (37 1 g 0 371 mol) in water (32 ml) was added dropwise with stirπng over 2 h The mixture was heated with stirπng for another 30 minutes, allowed to cool down to r t . and poured into water (1000 ml) The product was extracted with diethyl ether (3 x 200 ml) Combined ether layers were washed with water and evaporated to dryness The residue was dissolved in 10% aqueous potassium carbonate and washed with ether The aqueous layer was acidified with con HC1. and the resulting white precipitate filtered and dπed ( 16 3 g. 83%). m p 174- 177 °C rerf-Butyl 2-fluoro-4-nιtrobenzoate Thionyl chloπde (45 ml. 0 62 mol) was added to 2-fluoro-4-nιtrobenzoιc acid (23 0 g, 0 124 mol), and the mixture was stirred under reflux for 2 h Solvent was removed under vacuum, and the residue thoroughly dπed under vacuum to give crystalline acid chloπde (25 2 g, 99%) The acid chloπde was dissolved in tetrahydrofuran (150 ml) under nitrogen, and 1M lithium tert-butoxide in tetrahydrofuran (136 ml, 0 136 mol) was added dropwise with stirπng at room temperature The mixture was stirred overnight, diluted with water (300 ml ) and extracted with ether The ether layer was washed with saturated aqueous sodium bicarbonate, bπne. and dπed (MgS0 4 ) Solvent was removed under vacuum to gave the product as a white crystalline solid (24 2 g. 81%), mp 81-82 °C fgrf-Butyl-2-fluoro-4-amιnobenzoate 7>rr-butyl 2-fluoro-4-nιtrobenzoate (24 2 g. 0 100 mol) was added to a warm (95°C) solution of ammonium chloπde (53 5 g, 1 00 mol). dissolved in ethanol (300 ml) and water ( 150 ml) Iron powder (325 mesh. 16 8 g. 0 300 mol) was added with stimng in small portions over about 1 h The reaction mixture was stiπed and heated at 95°C for another 30 minutes and then filtered while still warm The filter cake was washed thoroughly with excess ethanol The filtrate and washings were diluted with water (1 L) and extracted with ether (3 x 150 ml) Combined ether extracts were washed with water and brine, dried (MgS0 4 ), and ev aporated to give the product as an off-white solid (21 1 g. 98%), mp 100- 101 °C 0-Benzyl-N-(3-fluoro-4-butoxycarbonylphenyl)carbamate Benzyl chlorotormate ( 15 9 ml. 0 1 12 mol) was added dropwise with stimng to a mixture of rerr-butyl-2-fluoro-4-amιnobenzoate (21 5 g. 0 102 mol) and pyπdine ( 16 5 ml. 0 204 mol) in dichloromethane (200 ml) at 0 °C The reaction mixture was stirred for 30 minutes at 0 °C. allowed to warm up to room temperature, and then poured into water (about 300 ml) The organic layer was separated, washed with water, brine and dned (MgS0 4 ) Evaporation gave a hite solid, which was washed with hexane and dπed under vacuum to afford the product (32 8 g, 93%). mp 1 17- 1 18°C 5-(R)-Hydroxymethyl-3-f4'-fer7-butoxycarbonyl-3'- fluorophenylloxazolιdιne-2-one 1M Lithium bιs(tπmethylsιlyl)amιde in tetrahydrofuran ( 104 ml. 0 104 mol) was added dropwise with stirπng at -78 °C to a solution of 0-benzyl-N-(3- fluoro-4-butoxycarbonylphenyl)-carbamate (32 8 g, 0 0948 mol) in tetrahydrofuran (150 ml) The mixture was stirred at -78°C for 1 hour, and then (R)-glycιdyl butyrate (15 0 g, 0 104 mol) was added dropwise with stimng The mixture was allowed to warm to room temperature overnight, and was then quenched with saturated aqueous ammonium chloπde ( 100 ml) The mixture was extracted with ethyl acetate, and the combined organic layers washed with water, bnne. and dned (MgS0 4 ) Solvent was removed under vacuum, and the crude product punfied by silica gel column chromatography (eluent 30% ethyl acetate in hexanes) to afford the product as a white solid (20 0 g. 68%). mp 148-149 °C 5-(S)-Azιdomethyl-3-[4'-fgrf-butoxycarbonyl-3'-fluorophenylloxazohdιne- 2-one Methanesulfonyl chlonde (2 61 ml. 0 0337 mol) was added dropwise with stirπng to a solution of 5-(R)-hydroxymethyl-3-[4'-r -butoxycarbonyl-3'- fluorophenyl]oxazohdιne-2-one (10 0 g. 0 0321 mol) and tπethylamine (6 71 ml. 0 0482 mol) in dichloromethane (150 ml) at 0 °C over about 15 minutes The reaction mixture was allowed to warm up to room temperature and then poured into water The organic layer was separated washed with water saturated aq NaHCOi brine, and dried (MgS0 4 ) Solvent was removed under vacuum to afford the mesylate intermediate as an oil ( 1 1 6 g. 99%) A mixture of the mesylate ( 13 4 g. 00370 mol) and sodium azide (12 0 g. 0 185 mol) in DMF (130 ml) was heated with stirnng at 75 °C for 12 h The reaction mixture was cooled to room temperature, diluted with water (300 ml), and extracted with ethyl acetate (3 x 100 ml) Combined organic layers were washed with water and bπne, dned (MgS0 4 ) and evaporated The residue was washed with diethyl ether to give the pure azide as a white solid (9 76 g, 90 5%). mp 91-92 °C Example 3 5-(S)-Azιdomethyl-3-[4'-chlorocarbonyl-3'-fluorophenylloxazolιdιne-2- one 60% TFA in DCM (5 mL) was added to 5-(S)-azιdomethyl-3-[4'-r<?rr- butoxycarbonyl-3'-fluorophenyl]oxazohdιne-2-one (0 336 g, 1 mmol), and the solution kept at r t for 1 h Solvents were removed in vacuo to afford 5-(S)- azιdomethyl-3-[4'-carboxy-3'-fluorophenyl-]oxazohdιne-2-one dned (0 280 g, 99%) N-Tπmethylsilyl-N.N-diethylamine (0 23 mL. 1 2 mmol) was added to above product in dry dichloromethane (3 mL) under nitrogen atmosphere, and the solution stirred for 15 min Solvents and excess reagent were removed in vacuo. and residue dissolved in dichloromethane (4 mL) The solution was cooled to about 0 °C, and oxalyl chloπde (1 5 mmol, 0 13 mL) was added dropwise. followed by catalytic N.N-dimethylformamide (about 0 01 mL) The mixture was alllowed to warm up to r t (room temperature), and stirred at r t for another 2 h Solvents were removed in vacuo to afford the product as a white solid Yield 0 292 g (98%) 5-(S)-Azιdomethyl-3-[4'-(6"-chloropyndιne-3"-yl)ammocarbonyl-3 ' - fluoro-phenylloxazolιdιne-2-one 5-(S)-Azιdomethyl-3-[4'-chlorocarbonyl-3'-fluorophenyl]oxazohdιne-2- one (0 298 g. 1 0 mmol) was added to a solution of 5-amιno-2-chloropyπdιne (0 129 g, 1 0 mmol) in 20% pyndine in THF (2 mL), and the mixture stirred at r t overnight Solvent was removed unde vacuum, and the residue triturated with water Resulting crude product was washed with 3% aq. citric acid. 2% aq. sodium bicarbonate, water, ethyl ether, and dried under vacuum (yield 0.357 g. 917c; 'H NMR). 5-(S)-Amιnomethyl-3-|4 ' -(6"-chloropyπdιne-3 " -yl )amιnocarbonyl-3 ' - flυoro-phenylloxazohdιne-2-one. 5-(S)-Azιdomethyl-3-[4 ' -(6 "" -chloropyπdιne-3 * '-yl)ammocarbonyl-3 ' - fluoro-phenyl]oxazohdιne-2-one (0.35 g. 0.896 mmol) and tnphenylphosphine (0.235 g. 0.896 mmol) in THF ( 10 mL) was stiπed at r.t. for 4 h and then at 40 °C for 2 h. Water (0.5 mL) was added, and the mixture stiπed at 40°C overnight. Solvents were removed in vacuo, and resulting crude product washed with ethanol and diethyl ether. Yield 0.215 g (66%) Η NMR. MS (m/z): [M+H] + = 365. 5-(S)-Thιoacetamιdomethyl-3-[4'-(6"-chloropyrιdιne-3"- yl)aminocarbonyl-3 ' -fluoro-phenynoxazolidine-2-one. This compound was prepared analogously to Method A (Example 1 ) above from 5-(S)-amιnomethyl-3-[4'-(2"-chloropyndιne-5"-yl)amιnocarbonyl-3 ' - fluorophenyl]oxazohdine-2-one (0.125 g, 0.343 mmol) and ethyl dithioacetate. The crude product purified by PTLC ( 10% MeOH in DCM). Yield 0.035 g (24%). MS (m z): [M+Hf = 421. Example 4 5-(S)-Azιdomethyl-3-I4 ' -(5"-trιfluoromethylpyπdιne-2"- yl )amιnocarbonyl-3'-fluorophenylloxazohdιne-2-one This compound was prepared analogously to the synthesis of 5-(S)- azιdomethyl-3-[4'-(6"-chloropyπdιne-3"-yl)amιnocarbonyl-3'- fluorophenyl]oxazohdιne-2-one from 2-amιno-5-tπfluoromethylpyπdιne (0 100 g, 0 62 mmol) and 5-(S)-azιdomethyl-3-[4'-chlorocarbonyl-3'- fluorophenyl]oxazohdιne-2-one (0 184 g, 0 62 mmol) Yield 0 11 g (427c) MS (m z) [M+H] + = 425 5-(S)-Amιnomethyl-3-[4 ' -(5 " -trιfluoromethylpyπdιne-2"- \ l )amιnocarbonyl-3 ' -fluorophenvnoxazohdιne-2-one Preparation was analogous to the synthesis of 5-(S)-amιnomethyl-3-[4'- (6 " -chloropyπdιne-3"-yl)amιnocarbonyl-3'-fluorophenyl]oxazohdιne-2-one from 5-(S)-azιdomethyl-3-[4'-(5"-tπfluoromethylpyπdιne-2"-yl)amιnocarbonyl-3 ' - fluorophenyl]oxazohdιne-2-one (0 100 g, 0.235 mmol) and tnphenylphosphine (0 068 g, 0 259 mmol) Yield 0 087 g (93%) MS (m/z) [M+H] + = 399 5-(S)-Thιoacetamιdomethyl-3-f4'-(5"-tnfluoromethylpyπdιne-2 " - yl)amιno-carbonyl-3'-fluorophenvπoxazohdιne-2-one This compound was prepared analogously to the Method A of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones (Example 1) from 5-(S)-ammomethyl-3-[4'-(5"-tπfluoromethylpyndιne-2"-yl)amιnocarbonyl- 3'-fluorophenyI]oxazohdme-2-one (0 070 g, 0 176 mmol) and ethyl dithioacetate The crude product was punfied by PTLC (10% MeOH m DCM) Yield 0 020 g (20%) MS (m z) [M+H] + = 457 Example 5 5-(S)-Azιdomethyl-3-[4 ' -(5"-tπfluoromethyl- l".3".4"-thιadιazole-2 "' - yl)amιno-carbonyl-3 ' -fluorophenylloxazohdιne-2-one. Prepared analogously to the synthesis of 5-(S)-azιdomethyl-3-[4 ' -(6 " - chloropyπdιne-3"-yl)amιnocarbonyl-3'-fluorophenyl]oxazohdιne-2-one trom 2- amιno-5-tπfluoromethyl-1.3.4-thιadιazole (0 100 g, 0.59 mmol) and 5-(S)- azιdomethyl-3-[4'-chlorocarbonyl-3 ' -fluorophenyl]oxazohdιne-2-one (0 176 g. 0 59 mmol) Yield 0.093 g (36%) MS (m z). [M+H] + = 432 5-(S)-Amιnomethyl-3-f4'-(5"-tπfluoromethyl-l".3".4"-thιadιazole-2"- yl)amι-nocarbonyl-3'-fluorophenylloxazolιdιne-2-one Prepared analogously to the synthesis of 5-(S)-amιnomethyl-3-[4 ' -(6"- chloropyrιdιne-3"-yl)amιnocarbonyl-3'-fluorophenyl]oxazohdιne-2-one from 5- (S)-azιdomethyl-3-[4'-(5"-tπfluoromethyl-l".3".4"-thιadιazole-2"-yl)amιno- carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0 090 g, 0 209 mmol) and tnphenylphosphine (0.055 g, 0.209 mmol). Yield 0.010 g ( 12%) MS (m/z) [M+H] + = 406. 5-(S)-Thιoacetamιdomethyl-3-I4'-(5"-tπfluoromethyl-l".3".4"- thιadιazole-2"-yl)amιnocarbonyl-3'-fluorophenylloxazolιdιne-2-one Prepared analogously to the Method A of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones (Example 1) from 5-(S)-amιnomethyl- 3-[4 ' -(5"-tπfluoromethyl-l".3",4"-thιadιazole-2"-yl)amιnocarbonyl-3'- fluorophenyl]-oxazohdιne-2-one (0.010 g, 0.0247 mmol, prepared analogously to U S. Pat. 09/235,771) and ethyl dithioacetate The crude product purified by PTLC ( 10% MeOH in DCM) Yield 0.0035 g (31%) MS (m z)- [M+Hf = 464 Example 6 3-Fluoro-4-thιocyanoanιlιne N-Bromosuccinimide ( 1.76 g. 9 89 mmol) and potassium thiocyanate ( 1 75 g. 18.0 mmol) in methanol (30 ml) were stiπed for 15 minutes at room temperature. The reaction mixture was cooled to 0°C. and 3-fluoroanιhne (1 00 g. 9 0 mmol) was added dropwise. The mixture was stiπed at 0°C for 2 h. Solvent was removed under vacuum, and the residue was washed with dichloromethane. The mixture was filtered to remove succimmide by-product, and the solution was washed with water, bnne. and dned (MgS0 4 ). Solvent was removed under vacuum to afford the desired product as a colorless oil Yield 1.45 g (96%) Q-Benzyl-N-r3-fluoro-4-(thιocyano)phenyllcarbamate. Benzyl chloroformate (1.87 ml. 13.1 mmol) was added to a mixture of 3- fluoro-4-thιocyanoanιhne (2.00 g, 11 9 mmol) and pyndme (2.12 ml. 26.2 mmol) in dichloromethane (30 ml) at 0 °C. The mixture was stiπed for 30 minutes at 0°C. allowed to warm to room temperature, and then poured into water The organic layer was separated, washed with bnne, and dned (MgS0 4 ). Solvent was removed under vacuum. The crude product was washed ith ether-hexanes and dned under vacuum to afford the desired product. Yield 3.64 g (92%); m.p 74-75 °C. 0-Benzyl-N-r3-fluoro-4-(tnphenylmethylthιo)phenyllcarbamate. Sodium sulfide nonahydrate (0.794 g, 3.31 mmol) in water (3 ml) was added dropwise at room temperature to a solution of 0-benzyl-N-[3-fluoro-4- (thιocyano)phenyl]carbamate (1.00 g. 3.31 mmol) in ethanol (10 ml). The reaction mixture was stiπed at room temperature for 30 minutes, and then tnphenylmethyl bromide (1 07 g. 3.31 mol) in 1.4-dιoxane (5 ml) was added dropwise. The reaction was stiπed overnight. Organic solvent was removed under vacuum, and the residue taken up in ethyl acetate The solution was washed with water, bnne. and dried (MgS0 ). Solvent was removed under vacuum, and the crude product punfied by silica gel column chromatography (eluent: 10% ethyl acetate in hexanes) to give the desired compound as a white solid. Yield 1.10 g. (64%): mp 152-153 °C 5-(R)-Hvdro\vmethyl-3-|4'-tπphenylmethylthιo-3'- fluorophenyl |oxazohdιne-2-one 1 M Lithium lsιly!)amιde in tetrahydrofuran (54 mL. 69 9 mmol ) was added dropwise with stimng at -78 °C to a solution of 0-benzyl-N-[3- fluoro-4-(trιphenylmethylthιo)phenyl]carbamate (33.0 g. 63 5 mmol) in tetrahydrofuran (250 ml ) The mixture was stiπed at -78 °C for 1 hour, and then (R)-glycιdyl butyrate ( 1 1 0 g. 76.2 mmol) was added dropwise with stiπing. The mixture was allowed to warm up to room temperature overnight, and then quenched with saturated aq. ammonium chloride ( 125 ml). The mixture was extracted with ethyl acetate, and combined organic layers washed with water, brine, and dried (MgS0 4 ) Solvent was removed under vacuum, and the crude product punfied by silica gel column chromatography (gradient from 30% to 75% of ethyl acetate in hexane ) to afford the product. TLC R f 0 2 (ethyl acetate- hexanes 1 : 1 ). MS 486 [M+Hf 5-(S -Azιdomethyl-3-f4'-trιphenylmethylthιo-3'-fluorophenylloxaz.ohdιne- 2-one. Methanesulfonyl chloπde (3 91 mL. 50.6 mmol) was added dropwise with stirπng to a solution of 5-(R)-hydroxymethyl-3-[4'-tπphenylmethylthιo-3 ' - fluorophenyl]oxazohdιne-2-one (23.4 g, 48.2 mmol) and tπethylamine ( 10.1 mL. 73.8 mmol) in dichloromethane (200 mL) at 0 °C over about 10 minutes. The reaction mixture was allowed to warm up to room temperature and then poured into water. The organic layer was separated, washed with water, saturated aq. NaHC0 . bnne, and dπed (MgS0 4 ). Solvent is removed under vacuum to afford the mesylate intermediate as an oil (27.2 g, 99%) The mesylate (27.2 g, 48.2 mmol) and sodium azide ( 15.7 g, 241.0 mmol) in DMF (150 ml) was heated with stimng at 70 °C for 12 h. The reaction mixture was cooled to r.t.. diluted with water (750 mL). and extracted with ethyl acetate. Combined organic layers were washed with water, brine, and dπed (MgS0 ) Solvent was removed under vacuum and the crude product punfied by silica gel column chromatography (eluent: 30% ethyl acetate in hexanes) to afford the azide product as a white solid. Yield 18.1 g (73%) M.p 77-79 °C. 5-(S)-Amιnomethyl-3-f4 ' -tπphenylmethylthιo-3'- fluorophenylloxazohdιne-2-one. Tnphenylphosphine (2.82 g. 10.8 mmol) was added portionwise to a solution of 5-(S)-azιdomethyl-3-[4'-tπphenylmethylthιo-3 ' - fluorophenyl]oxazohdιne-2-one (5.00 g, 9.79 mmol) in THE (40 mL), and the mixture stiπed for 2 h at r.t.. Water ( 1.41 mL. 78.3 mmol) was added, and the mixture heated at 40 °C overnight. Solvent was removed under vacuum, and the oily residue punfied by column chromatography (eluent: DCM, then 10% MeOH in DCM). Yield 3.56 g (75%). MS (m z): [M+H] + = 485. 5-(S)-Acetamidomethyl-3-[4'-tnphenylmethylthio-3'- fluorophenylloxazohdιne-2-one. Tnphenylphosphine (2.82 g. 10.8 mmol) was added portionwise to a solution of 5-(S)-azιdomethyl-3-[4'-tnphenylmethylthιo-3'- fluorophenyl]oxazohdιne-2-one (5.00 g. 9.79 mmol) in THF (40 mL). and the mixture stiπed for 2 h at room temperature. Water (1.41 mL, 78.3 mmol) was added, and the mixture heated at 40 °C overnight. Solvent was removed under vacuum, and the oily residue dissolved in dichloromethane (50 mL). Acetic anhydride (4.62 ml, 49.0 mmol) and pyndine (7.92 ml. 97.9 mmol) were added, and the mixture stiπed for 8 h at r.t. Solvent was removed under vacuum and the crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes) to give the product as a foam (4.98 g, 97 %); MS (m/z). [M+H] + = 527. General Procedure for Preparation of 5-(S)-(N-Acylamιnomethyl)-3-[4'- (substιtuted)thιo-3'-fluorophenylloxazohdme-2-ones. 57c TFA and 2.57c trnsopropylsilane in dichloromethane (2.0 mL) was added to 5-(S)-acetamιdomethyl-3-[4'-tnphenylmethylthιo-3'- fluorophenyl]oxazoh-dιne-2-one (0.10 g. 0.19 mmol), and the mixture was stiπed at r t. for 1 h. and the mixture stiπed for 1 h at room temperature. Solvent was removed under vacuum, and the residue dissolved in methanol (3 mL). An appropπate alkylating or (hetero)arylatιng reagent ( 19-0.38 mmol) was added, followed by dropwise addition of 4.37 M sodium methoxide in methanol (0.087 ml. 0 380 mmol). Optionally, an organic base was used instead of sodium methoxide (e g , tetramethylguanidine or alkylamine) The mixture was stiπed at 20-70 °C for 2-24 h (typically. 2 h at r t ) Solvent was removed under vacuum and the crude product purified by TLC (methanol-dichloromethane mixtures) Example 7 5-(S)-Acetamιdomethyl-3-[4'-(2"-chloroethyl)thιo-3'- fluorophenylloxazohdi-ne-2-one Prepared according to the General Procedure for Preparation of 5-(S)-(N- Acylamιnomethyl)-3-[4'-(substιtuted)thιo-3 ' -fluorophenyl]oxazohdιne-2-ones (Example 6) from 5-(S)-acetamιdomethyl-3-[4 ' -(tnphenylmethyl)lthιo-3 ' - fluorophenyl]-oxazohdιne-2-one with l-bromo-2-chloroethane (0 055 g. 0 38 mmol) in N-methylpyπohdme-2-one ( 1 mL) The synthesis was performed at r t for 2 h The crude product was punfied by TLC (eluent 107c methanol in dichloromethane) Yield 0 047 g (727c) MS (m z) 347 [M+H] + 5-(S)-Thioamidomethyl-3-r4'-(2"-chloroethyl)thio-3'-fluorophenvHoxazo- lιdme-2-one Prepared analogously to the Method B of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazolιdιnones (Example 1 ) from 5-(S)- acetamιdomethyl-3-[4'-(2"-chloroethyl)thιo-3'-fluorophenyl]oxazohdιne-2-one (0 0275 g. 0 0793) and Lawesson reagent Yield 0 027 g (947c) M p 134-5 °C MS (m z) [M+H] + = 363 Example 8 5-(S)-Acetamιdomethyl-3-f4'-(5 " -nιtrothιazole-2 ' -yl)thιo-3 ' - fluorophenyll-oxazohdιne-2-one Prepared according to the General Procedure for Preparation of 5-(S)-(N- Acylamιnomethyl)-3-[4 ' -(substιtuted)thιo-3 ' -fluorophenyl]oxazohdme-2-ones (Example 6) from 5-(S)-acetamιdomethyl-3-[4'-(tπphenylmethyl)lthιo-3'- fluorophenyl]-oxazohdιne-2-one with 2-bromo-5-nιtrothιazole (0 079 g, 0 38 mmol) in N-methylpyπohdιne-2-one (1 mL) The synthesis was performed at r t for 2 h The crude product was purified by TLC (eluent 107c methanol in dichloromethane) Yield 0 061 g (78%) MS (m z) 413 [M+H] + 5-(S)-Thιoamιdomethyl-3-[4'-(5"-nιtrothιazole-2"-yl)thιo-3 ' - fluorophenyll-oxazolιdιne-2-one Prepared analogously to the Method B of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones (Example D from 5-(S)- acetamιdomethyl-3-[4'-(5"-nιtrothιazole-2"-yl)thιo-3'-fluorophenyl]oxazohdιne- 2-one (0 028 g, 0 0736 mmol) and Lawesson reagent Yield 0 026 g (837o) M p 1 16-7 °C MS (m/z) [M+H] + = 429 Example 9 5-(S)-AcetamιdomethyI-3-(4'-methylthιo-3'-fluorophenyl)oxazolιdιne-2- one Prepared according to the General Procedure for Preparation of 5-(S)-(N- Acylammomethyl)-3-[4'-(substιtuted)thιo-3'-fluorophenyl]oxazohdιne-2-ones (Example 6) from 5-(S)-acetamιdomethyl-3-[4'-(tnphenylmethyl)lthιo-3'- fluorophenyl]-oxazohdme-2-one with methyl iodide (0 05 mL. 0 81 mmol) in N- methylpyπohdme-2-one (1 mL) The synthesis was performed at r t overnight, and the crude cleaved product punfied by TLC (eluent 10% methanol in dichloromethane) Yield 6 3 mg (527c) MS 299 [M+H] + 5-( S)-Thιoamιdomethyl-3-[ 4 ' -methylthιo-3 ' -fluorophenyl ]-oxazolιdιne-2- one Prepared analogously to the Method B (Example 1 ) of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones from 5-(S)- acetamιdomethyl-3-[4 ' -methylthιo-3'-fluorophenyl]oxazohdιne-2-one (0 100 g, 0 335 mmol ) and Lawesson reagent Yield 0 095 g (907c) M.p. 130- 1 °C MS (m/z ) [M+H1 + = 315 Example 10 5-(S)-Thιoamιdomethyl-3-[4'-(tπphenylmethl)thιo-3 ' - fluorophenylloxazoh-dιne-2-one. Prepared analogously to the Method A of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdmones (Example 1) from 5-(S)-amιnomethyl- 3-[4 ' -(tπphenylmethyl)thιo-3'-fluorophenyl]-oxazohdme-2-one (0.500 g, 1.03 mmol, prepared analogously to U.S. Pat. 09/235,771) and ethyl dithioacetate Reaction performed in DCM overnight Yield 0 498 g (897c). MS (m/z): [M+Hf = 543 Example 11 5-(S)-Acetamιdomethyl-3-f4'-(2"-hvdroxyethyl)thιo-3 ' - fluorophenylloxazo-hdιne-2-one Prepared according to the General Procedure for Preparation of 5-(S)-(N- Acylamιnomethyl)-3-[4 ' -(substιtuted)thιo-3'-fluorophenyl]oxazoh-dιne-2-ones (Example 6) from 5-(S)-acetamιdomethyl-3-[4 ' -(tπphenylmethyl)lthιo-3 ' - fluorophenyl l-oxazohdιne-2-one with 2-bromoethanol (0 048 g. 0 38 mmol ) in N- methylpyπohdιne-2-one ( 1 mL) The synthesis was performed at r t for 2 h The crude product was purified by TLC (eluent 107c methanol in dichloromethane) Yield 0 045 g (727c) MS (m/z) 329 [M+H] + 5-(S)-Thιoamιdomethyl-3-f4'-(2"-hvdroxyethyl)thιo-3 ' - fluorophenylloxazo-hdιne-2-one A solution of 5-(S)-thιoamιdomethyl-3-[4'-(tnphenylmethyl)thιo-3 " - fluorophenyl]oxazohdιne-2-one (0 100 g, 0 184 mmol) in 5% TFA and 2 57c tnisopropylsilane in DCM (2 mL) is stiπed at r t for 1 h Solvent is removed under vacuum, and the residue is dissolved in THF (2 mL) 2-Bromoethanol (0 0196 ml. 0 276 mmol) is added followed by tnethylamine (0 0513 mL. 0 368 mmol) The reaction is stiπed at r.t for 2h. diluted with ethyl acetate, washed with water, brine, and dned Solvent is removed under vacuum and the residue is punfied by PTLC ( 10% MeOH in DCM) to give the product Example 12 5-(S)-Amιnomethyl-3-[4'-(fert-butoxy)carbonyl-3'- fluorophenvnoxazohdιne-2-one A mixture of tnphenylphosphine (0 521 g. 1 99 mmol) and 5-(S)- azιdomethyl-3-[4'-(rerr-butoxy)carbonyl-3'-fluorophenyl]]oxazohdme-2-one (0 607 g. 1 80 mmol) in THF (10 ml) was stiπed at r t. for 2 h. Water (0.259 ml. 14 4 mmol) was added, and the mixture was heated at 40 °C overnight The reaction mixture was evaporated, the residue taken up in ethyl acetate (20 mL) and extracted with 3% aqueous citnc acid (3 x 25 ml) Combined aqueous extracts were neutralized with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate Combined organic layers were washed with brine, dried (MgS0 ), and evaporated to give the product as a white solid (0.62 g. 99 7c) MS (m/z) [M+H] + = 31 1 5-(S)-Thιoacetamιdomethyl-3-[4'-(fgrr-butoxy)carbonyl-3'- fluorophenylloxazo-lιdιne-2-one. A solution of 5-(S)-amιnomethyl-3-[4'-(?err-butoxy)carbonyl-3'- fluorophenyl]- oxazohdιne-2-one (3.00 g, 9.66 mmol), tnethylamine ( 1.35 ml. 19.3 mmol), and ethyl dithioacetate (1.22 ml. 10.6 mmol) in DMF (8 mL) was stiπed at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate ( 50 ml), washed with 37o aqueous citric acid (3 x 30 mL). saturated aqueous sodium bicarbonate (30 mL), brine, and dried (MgS0 4 ). Evaporation afforded the product as a white solid (3.00 g. 847o). MS (m z): [M+H] + = 369. Example 13 5-(S)-Thιoacetamιdomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazohdιne-2- one. 5-(S)-Thιoamιdomethyl-3-[4'-(rerr-butoxy)carbonyl-3'- fluorophenyl]oxazolidι-ne-2-one (2.50 g, 6.79 mmol) was dissolved in 507c TFA/DCM (30 mL) and stiπed for 1 h at r.t. Solvents were removed under vacuum to afford the product as a white solid (2.12 g, 997c). M.p. 180-2 °C. MS (m/z): [M+H] + = 313. Example 14 5-(S)-Thιoacetamιdomethyl-3-[4'-(thιazole-2"-yl)amιnocarbonyl-3 ' - fluorophenylloxazohdιne-2-one. A solution of 5-(S)-thιoacetamιdomethyl-3-(4 ' -carboxy-3 ' -fluorophenyl)- oxazohdιne-2-one (0 037 g, 0.120 mmol). 0-(7-azabenzotπazol-l-yl)-N. N. N'. N ' -tetramethyiuronium hexafluorophosphate (0.0502 g. 0 132 mmol ). and DIEA (0.0627 mL. 0 360 mmol) in DMF (0 5 mL) was stiπed at r.t. for 20 minutes. 2- Aminothiazole (0.0120 mg, 0.120 mmol) was added and the mixture stiπed overnight. Most of the solvent was removed under vacuum and the residue purified by preparative HPLC to give pure product as a white solid (0.020 mg. 427c). MS (m/z): [M+H] + = 395 Example 15 5-(S)-Thιoacetamιdomethyl-3-[4'-(thιazole-2"-yI)amιnothιocarbonyl-3 ' - fluorophenylloxazolιdιne-2-one A mixture of 5-(S)-thιoacetamιdomethyl-3-[4'-(thιazole-2"- yl)amιnocarbonyl-3'-fluorophenyl]oxazohdιne-2-one (0.040 g, 0.10 mmol) and Lawesson reagent (0.020 g, 0.05 mmol) in dioxane (0.5 mL) is stiπed at 60-70 °C overnight. Solvent is removed under vacuum and the crude product is punfied by PTLC. Example 16 5-(S)-Thιoacetamιdomethyl-3-f4'-(pentafluorophenoxy)carbonyl-3'- fluorophenylloxazohdine-2-one. A mixture of 5-(S)-thιoamιdomethyl-3-(4'-carboxy-3'- fluorophenyl)oxazol-ιdιne-2-one (0 650 g. 2.08 mmol), pyndine (0.673 ml. 8 32 mmol). and pentafluorophenyl trifluoroacetate (0.429 ml. 2.50 mmol) in DMF (8 mL) was stiπed at r.t. for 3 h. The reaction mixture was diluted with ethvl acetate, w shed with 3% aqueous citric acid, brine, and dried (MgS0 4 ) Evaporation afforded the pure product as a white solid (0.90 g. 907c ) M p. 163-4 Example 17 5-(S)-Thιoacetamιdomethyl-3-[4 ' -(N-methylamιno)carbonyl-3 ' - fluorophenyll-oxazohdιne-2-one. A solution of 5-(S)-thιoacetamιdomethyl-3-[4'- (pentafluorophenoxy)carbonyl-3 ' -fluorophe-nyl]oxazohdιne-2-one (0.100 g. 0.209 mmol) in 2 M methylamine in THF ( 1.0 mL) was stiπed at r.t. for 1 h. Solvent was removed under vacuum and the residue purified by PTLC (10% MeOH in DCM) to give the pure product as a white solid (0.054 g. 807c). M.p. 176-7 °C. MS (m/z): [M+H] + = 326. Example 18 5-(S)-Thιoacetamιdomethyl-3-[4 ' -methoxycarbonyI-3 ' - fluorophenylloxazolι-dιne-2-one A solution of 5-(S)-thιoacetamιdomethyl-3-[4'- (pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0.100 g. 0.209 mmol) and 257c sodium methoxide in methanol (0.0573 ml. 0.251 mmol) in methanol (2 mL) was stiπed at r.t. for 1 h solvent was removed under vacuum and the residue purified by PTLC ( 107c MeOH in DCM) to give the pure product as a white solid (0.057 g. 847c). M p 152-4 °C MS (m/z): [M+Hf = 327. Example 19 5-(S)-Thιoacetamιdomethyl-3-[4'-(ιmιdazole-2"-yl)amιnocarbonyl-3 ' - fluoro-phenyll-oxazohdιne-2-one. A solution of 5-(S)-thιoacetamιdomethyl-3-[4 ' - (pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0 162 g, 0.34 mmol) and 2-amιnoιmιdazole (0.083 mg, 1.0 mmol) in THF (5.0 mL) was stiπed at r.t for 0.5 h and then at 45 °C overnight. Solvent was removed under vacuum and the residue purified by PTLC ( 107c MeOH in DCM) to give the pure product as a white solid (0.058 g. 457c). MS (m/z): [M+H] + = 378. Example 20 5-(S)-Thιoacetamιdomethyl-3-[4'-(ιmιdazole-2"-yl)thιoamιnocarbonyl-3'- fluorophenyll-oxazolidιne-2-one. A mixture of 5-(S)-thιoacetamιdomethyl-3-[4'-(ιmιdazole-2"-yl)ammo- carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0.038 g, 0.10 mmol) and Lawesson reagent (0.020 g, 0.05 mmol) in dioxane (0.5 mL) is stiπed at 60-70 °C overnight. Solvent is removed under vacuum and the crude product is punfied by PTLC. Example 21 5-(S)-Azιdomethyl-3-f4'-(f -butoxycarbonyl)amιno-3'-fluorophenvH- oxazohdιne-2-one. TFA (30 mL) was added to a solution of 5-(S)-azιdomethyl-3-[4 ' -(r<?rr- butoxy)carbonyl-3'-fluorophenyl]oxazolidme-2-one (6.72 g. 20 mmol) in DCM (20 mL). and the solution was kept at r.t. for 1 h. Solvents were removed under vacuum to afford 5-(S)-azιdomethyl-3-(4'-carboxy-3'-fluorophenyl )oxazolιdιne-2- one THF (75 mL) was added, followed by t-butanol (9.5 mL. 100 mmol ). tπethylamine (3.6 mL. 26 mmol). and diphenylphosphoryl azide (5 6 mL. 26 mmol) The mixture was stiπed at r.t. under nitrogen atmosphere for 2 h. and then at 70 °C overnight. Solvent was removed under vacuum, and the residue distributed between ethyl acetate ( 150 mL) and aq. saturated sodium bicarbonate ( 100 mL) Aq. phase was washed with ethyl acetate (2 x 50 mL). Combined organic layers were washed with aq. saturated sodium bicarbonate, water, brine, and dried (MgS0 4 ). Solvent was removed under vacuum, and the product punfied by silica gel column chromatography (eluent: DCM). Yield 4.1 g (587c). MS (m/z)- [M+H] + = 352. 5-(S)-Amιnomethyl-3-[4 ' -(fgrf-butoxycarbonyl)amιno-3 ' -fluorophenyll- oxazohdιne-2-one. A mixture of tnphenylphosphine (0.521 g. 1.99 mmol) and 5-(S)- azιdomethyl-3-[4'-(rerr-butoxycarbonyl)amιno-3'-fluorophenyl]]oxazohdιne-2- one (0.632 g. 1.80 mmol) in THF (10 ml) was stiπed at r.t. for 2 h. Water (0.259 ml. 14 4 mmol) was added, and the mixture was heated at 40 °C overnight. The reaction mixture was evaporated, the residue taken up in ethyl acetate (20 mL) and extracted with 37c aqueous citnc acid (3 x 25 ml). Combined aqueous extracts were neutralized with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. Combined organic layers were washed with bnne. dned (MgS0 4 ). and evaporated to give the product as a white solid (0.53 g. 90 7c). MS (m z): [M+H] + = 326. 5-(S)-Acetamidomethyl-3-r4' -amino -3'-fluorophenylloxazohdine-2-one. Acetic anhydnde (0.15 mL) was added to a solution of 5-(S)-amιnomethyl- 3-[4 ' -(rerr-butoxycarbonyl)amιno-3'-fluorophenyl]oxazohdιne-2-one (0.325 g. 1.0 mmol) and pyndine (0.25 mL) in DCM (4.0 mL). The mixture was stiπed at r.t. for 4 h. and solvent was removed under vacuum. The resulted 5-(S)- jcetamιdomethyl-3-[4'-(rerr-butoxycarbonyl)ammo-3'-fluorophenyl]oxazoh-dιne- 2-one was washed with water (2 x 3 mL), diethyl ether (3 mL). and dned under v acuum. 507c TFA in DCM (3 mL) was added, and the mixture was kept at r.t. for lh. Solvents were removed under vacuum, and the residue distributed between ethyl acetate (40 mL) and saturated aq. sodium bicarbonate (20 mL) Organic layer was washed with aq sodium bicarbonate, water, brine, dried (MgS0 4 ) Solvent was removed under vacuum to afford the product as a hite solid Yield 0 25 g (957c) MS (m/z) [M+H] + = 268 5-(S)-Thιoacetamιdomethyl-3-f4 ' -amιno -3' -fluorophenyl loxazohdιne-2- one A mixture of 5-(S)-acetamιdomethyl-3-[4'-amιno-3 '-fluorophenyl ]oxazoh- dιne-2-one (0 100 g, 0 374 mmol) and Lawesson's reagent (0.151 g, 0 374 mol) in dioxane (2 ml) was stiπed at 65 °C for 2 h The solution was concentrated under vacuum and the residue purified by PTLC (107c methanol/dichloromethane) to give a tan solid (0 104 g, 987c), mp 137-88 °C, MS. (M+H) + = 284 Example 22 5-(S)-Thιoacetamιdomethyl-3-[4 ' -acetamιdo-3 '-fluorophenyl loxazohdine- 2-one A solution of 5-(S)-thιoacetamιdomethyl-3-[4'-amιno-3'- fluorophenyl]oxazoh- dιne-2-one (0.070 g. 0 247 mmol), acetic anhydnde (0 25 mL), pyndine (0 38 mL), and dichloromethane (0 75 mL) was stiπed at r t for 4 h Solvent was removed under vacuum and the crude prtoduct punfied by PTLC ( 107c MeOH in DCM) to give a white solid (0.076 g, 95%) M.p. 200- 1°C, MS (m/z) (M+H) + = 326 Example 23 5-(S)-Thιoacetamιdomethyl-3-[4 ' -(5"-nιtro-2"-furoyl)-3'- fluorophenyHoxazo-lιdιne-2-one 5-Nιtro-2-furoyl chloride (0.069 g, 0.392 mmol) in THF ( 1 mL) was added dropwise to a solution of 5-(S)-thιoacetamιdomethyl-3-[4'-amιno-3 ' - fluorophenyl]oxazohdιne-2-one (0.1 1 1 g, 0 392 mmol) and tnethylamine (0 109 ml. 0 784 mmol) in THF (3 mL) at 0 °C. The mixture was stiπed at r.t. for 1 h Ethyl acetate was added, and the mixture washed with water, saturated aq. sodium bicarbonate, brine, and dried (MgS0 4 ). Solvent was removed under vacuum, and the crude matenal punfied by PTLC (10% MeOH in DCM) to gave the pure product as an orange solid (0.079 g, 487c). M.p. 188-8 °C MS (m z). [M+H] + = 423 Example 24 5-(S)-Acetamιdomethyl-3-f4'-(l".2"3"-thιadιazole-4-yl)carbonylamιno-3' fluorophenylloxazolιdιne-2-one. A solution of l,2,3-thιadιazole-4-carboxyhc acid (0.0731 g, 0.562 mmol), thionyl chlonde (2 ml), and DMF (0.025 ml) was refluxed for 2 h. Solvent was removed under vacuum and the residue dissolved in THF (1 mL). Resulted solution was added dropwise at 0 °C to a solution of 5-(S)-acetamιdomethyl-3-[4'- amιno-3'-fluorophenyl]oxazohdιne-2-one (0.150 g, 0.562 mmol) and tnethylamine (0.157 mL, 1.12 mmol) m THF (3 mL), and the mixture stiπed for 1 h at r.t. The reaction mixture was diluted with ethyl acetate and washed with water, saturated aq. sodium bicarbonate, brine, and dned (MgS0 4 ). Evaporation and purification by PTLC ( 107c MeOH in DCM) gave pure product as a tan solid (0 132 g. 62% ). mp 233 ϋ C. MS ( M+Hf = 380 Example 25 5-(S)-Thιoacetamιdomethyl-3-[4 ' -( l".2"3"-thιadιazole-4- yl )carbonylamιno-3 ' -fluorophenyl ]oxazohdιne-2-one A mixture of 5-( S)-acetamιdomethyl-3-[4'-( l".2"3"-thιadιazole-4- yl (carbonyl- amιno-3 ' -fluorophenyl ]oxazohdιne-2-one. (0.0703 g. 0.185 mmol) and Lawesson ' s reagent (0.0374 g. 0.0925 mmol) in dioxane (3 mL) and sulfolane (0.02 mL) was stiπed at 65 °C for 2 h The solution was concentrated under vacuum, and the residue purified by PTLC ( 107c MeOH in DCM) to give a white solid (0.037 g. 517c). M.p. 203-4 °C. MS (m/z): [M+H] + = 396. Example 26 5-(S)-Acetamιdomethyl-3-f4'-formamιdo-3'-fluorophenyl]oxazolιdιne-2- one. A solution of 5-(S)-acetamιdomethyl-3-[4 ' -amιno-3'-fluorophenyl]- oxazohdιne-2-one (0.200 g. 0.748 mmol) , p-nitrophenyl formate (0.188 g. 1.12 mmol). and 2,6-dι-(rerr-butyl)pyndιne (0.336 mL. 1.50 mmol) in THF (4 mL) was stiπed at 65 °C overnight. Solvent was removed under vacuum and the residue punfied by PTLC (30% acetone in DCM) to give product as a white solid (0.188 g. 857c) M.p. 196-8 °C, MS (m/z): [M+H] τ = 296 5-(S)-Thιoacetamιdomethyl-3-f4 ' -foπnamιdo-3'- fluorophenylloxazolιdιne-2-one Prepared from 5-(S)-thιocetamιdomethyl-3-[4 ' -amιno-3'- fluorophenyl]oxazo-lιdιne-2-one (0 100 g, 0.353 mmol) as descnbed above for the synthesis of 5-(S)-acet-amιdomethyl-3-[4'-formamιdo-3'- fluorophenyl]oxazohdιne-2-one White solid (0 0979 g. 897c) M p 177-8 °C MS (m/z) [M+H] + = 312 Example 27 5-(S)-Acetamιdomethyl-3-r4'-methylamιno-3'-fluorophenylloxazohdιne- 2-one Methyl iodide (0.86 mL. 13.8 mmol) was added dropwise to the mixture of 5-(S)-azιdomethyl-3-[4'-(r -butoxycarbonyl)amιno-3'-fluorophenyl]oxazohdι- ne-2-one (1.6 g, 4.6 mmol) and LiH (0.1 10 g. 13.8 mmol) in dry DMSO (15 mL) The mixture was sonicated for lh at r.t.. and then stiπed oveπught. Water (200 mL) and diethyl ether (200 mL) were added, organic layer separated and aq phase washed with ether (2 x 100 mL). Combined organic layers were washed with water (5 x 200 mL). bnne. dned (MgS0 ). Solvent was evaporated under vacuujm to afford 5-(S)-azιdomethyl-3-[4' -(r -butoxycarbonyl)methylamιno-3 ' - fluorophenyl]oxazohdιne-2-one as a thick oil [yield 1 6 g (957c); MS (m/z) [M+H] + = 366] The intermediate was converted into 5-(S)-ammomethyl-3-[4'- (r^rr-butoxycarbonyl)methylamino-3'-fluoro-phenyl]oxazolidine-2-one with tnphenylphosphine ( 1.25 g, 4.8 mmol) as descnbed above for the synthesis of 5- (S)-amιnomethyl-3-[4'-(rert-butoxycarbonyl)methylamιno-3 ' - fluorophenyl]oxazohdιne-2-one. The resulted 5-(S)-amιnomethyl-3-[4'-(? - butoxycarbonyl)methylamιno-3'-fluoro-phenyl]oxazolιdιne-2-one was converted into 5-(S)-acetamιdomethyl-3-[4'-methylammo-3'-fluorophenyl]oxazohdιne-2- one via acetylation with acetic anhydnde followed by TFA deprotection as described above for the synthesis of 5-(S)-acetamιdomethyl-3-[4 ' -methylamιno- 3 " -fluorophenyl]-oxazohdιne-2-one. Yield 1.03 g (807c). R, 3 0 min. MS (m z) [M+H] + = 282. 5-(S)-Thιoacetamιdomethy 1-3-14 ' -methylamιno-3 ' - fluorophenvπoxazohdιne-2-one. A mixture of 5-(S)-acetamιdomethyl-3-[4'-methylamιno-3'-fluoro- phenyl]oxazolidιne-2-one (0.100 g. 0.356 mmol) and Lawesson reagent (0.144 g. 0.356 mmol) in dioxane (3 mL) was stiπed at 65 °C for 2 h. Solvent was removed under vacuum and the residue purified by PTLC ( 10% methanol/dichloromethane) to give a product as foam. Yield 0.097 g (927c). MS (m/z): [M+Hf = 298. Example 28 5-(S)-Thιoacetamιdomethyl-3-[4'-(N-methylformamido)-3'- fluorophenylloxa-zolidine-2-one. A mixture of 5-(S)-thιoacetamιdomethyl-3-[4'-methylammo-3 ' - fluorophenyl]-oxazolidine-2-one (0.100 g, 0.337 mmol) with p-nitrophenyl formate (0.084 g. 0.505 mmol), and (2.6-di-rert-butyl)pyridιne (0.151 mL, 0.674 mmol) in THF (4 mL) was stiπed at r.t. overnight. Solvent was removed under vacuum and the residue punfied by PTLC (30% acetone in DCM) to give product as a white solid (0.089 g. 827c). M.p. 105-7 °C. MS (m z): [M+H] + = 326. 5-(S)-Acetamidomethyl-3-[4'-(N-methylformamido)-3'-fluorophenyl]oxa- zohdιne-2-one. A solution of 5-(S)-acetamιdomethyl-3-[4'-rnethylamιno-3'- fluorophenyl]oxa-zohdine-2-one (0.200 g. 0.71 1 mmol) . p-nitrophenyl formate (0.178 g. 1.07 mmol). and 2.6-dι-tert-butylpyπdιne (0.319 mL. 1.42 mmol) in THF (4 mL) was stiπed at r.t. overnight. Solvent was removed under vacuum and the residue purified by PTLC (307c acetone/dichloromethane) to give product as a white solid (0.188 g, 857c). M.p. 1 16-7 °C; MS (m/z): [M+H] + = 310. Example 29 5-(S)-Thιocetamιdomethyl-3-14'-(N-methylthιoformamιdo)-3'- fluorophenyll-oxazolidine-2-one. A mixture of 5-(S)-acetamιdomethyl-3-[4'-(N-methylformamιdo)-3 ' - fluorophenyl]oxazolidme-2-one (0.100 g, 0.323 mmol) and Lawesson reagent (0.131 g. 0.323 mmol) in dioxane (3 mL) was stiπed at 65 °C for 2 hours. Solvent was removed under vacuum and the residue punfied by PTLC ( 107c MeOH in DCM) to give a white solid (0.101 g, 92%). M.p. 103-4 °C. MS (m/z): [M+H] + = 342. Example 30 5-(S)-Acetamidomethyl-3-r4'-(5".6"-dihvdro-l".4".2"-dioxazine-3"-yl)- 3'-fluorophenyl]oxazolidine-2-one. A solution of 5-(S)-acetamidomethyl-3-[4'-(N-hydroxyammo)carbonyl-3'- fluorophenyl]oxazohdιne-2-one (0.100 g, 0.321 mmol; prepared as descnbed in U.S. Pat. 09/235.771 ). cesium carbonate (0.209 g. 0.643 mmol), and 1.2- dibromoethane (0.0415 mL. 0.482 mmol) in l-methyl-2-pyπohdιnone (4 mL) was heated at 100 °C overnight. The reaction mixture w as diluted with ethyl acetate, washed with water, brine, dried (MgS0 4 ) Solvent was removed under vacuum, and the residue purified by PTLC ( 107c MeOH in DCM) to give product as a white solid (0.052 g, 48 7c). M p. 203-4 °C. MS (m/z). [M+Hf = 338 5-(S)-Thιoacetamιdomethyl-3- 4 ' -(5".6 " -dιhydro- l ".4".2"-dιoxazιne-3 " - yl)-3 " -fluorophenyl loxazohdιne-2-one A mixture of 5-( S)-acetamιdomethyl-3-[4 ' -(5".6"-dιhydro-l".4",2"- dιoxazιne-3"-yl )-3'-fIuorophenyl]oxazohdιne-2-one (0.040 g, 0.1 19 mmol) and Lawesson's reagent (0 0481 g. 0.1 19 mmol) in dioxane (2 mL) was stiπed at 65 °C for 2 hours, solvent was removed under vacuum and the residue purified by PTLC 107c MeOH in DCM) to give product as a white solid (0.034 g, 817c). M.p 166-7 °C: MS (m/z). [M+H] + = 354. Example 31 5-(S)-Thιoacetamιdomethyl-3-[4'-[N-methyl-(N-methylsulfonyl)amιnol- 3'-fluorophenyl]oxazohdιne-2-one. A mixture of 5-(S)-acetamιdomethyl-3-[4'-[N-methyl-(N-methylsulfonyl)- amιno]-3 ' -fluorophenyl]oxazohdιne-2-one (0.100 g, 0.279 mmol; prepared analogously to U.S. Pat 09/235.771) and Lawesson's reagent (0.113 g. 0.279 mmol) m dioxane (3 mL) was stiπed and heated at 65 °C for 2 h. Solvent was removed under vacuum and the residue punfied by PTLC ( 107c MeOH - DCM) to give a foam (0.090 g. 807c) MS (m/z): [M+Hf = 376 Example 32: Preparation and Use of Polymeric Thioacylating Agents Polymeric Thioacylating Reagent: Meπifield Resin Dithioacetate Carbon disulfide (0.725 mL. 0.0121 mol) was added dropwise with stiπing at r.t. to a solution of 3.0 M of methylmagnesium bromide in ether (3.09 mL. 9.27 mmol) in THF ( 15 mL), and the mixture stiπed for 3 h under nitrogen atmosphere. Meπifield resin (0.74 mmol/g. 2.5 g, 1.85 mmol) was added in one portion, and the reaction agitated overnight. The resin was filtered, washed liberally with THF. MeOH. DCM. and dried under vacuum. Thioamidation Using Meπifield Resin Dithioacetate. Meπifield resin dithioacetate (0.458 g. 0.339 mmol) and 5-(S)- aminomethyl-3-(4'-morphohno-3'-fluorophenyl)oxazohdine-2-one (0.020 g. 0 0677 mmol) in DMF (2 ml) were agitated at 65 °C for 4 hours. Supernatant was filtered off and the solvent removed under vacuum to afford 5-(S)- thιoamιdomethyl-3-(4'-morphohno-3'-fluorophenyl)oxazolidme-2-one. MS (m/z): [M+H] + = 354. Example 33 Solid Phase Thioamide Synthesis. A mixture of 5-(S)-amιnomethyl-3-(4'-morphohno-3'-fluorophenyl)- oxazolιdιne-2-one immobilized on BAL-hnker functionalized Tentagel polymer (0.21 g. 0.06 mmol) and Lawesson reagent (0.088 g, 0.217 mmol) in dioxane (3 mL) was agitated at 60 °C for 3 h. The resin was filtered, washed liberally with DMF. DMSO, DCM. MeOH, and dned under vacuum. 407c TFA in DCM (2 mL) added, and the mixture agitated for 1 h at r.t. Supernatant was filtered off. and solvents removed under vacuum to afford 5-(S)-thιoamιdomethyl-3-(4'- morphohno-3'-fluorophenyl)oxazolιdιne-2-one. Rt 3.8 min. MS (m/z): [M+H] + = 354 Example 34 5-(S)-Azιdomethyl-3-[4'-(5"-amιno- l".3".4"-thιadιazole-2"-yl)-3'-fluoro- phenyl]oxazolιdιne-2-one 607c TFA in DCM (5 mL) was added to 5-(S)-azιdomethyl-3-[4'-r - butoxycarbonyl-3 ' -fluorophenyl]oxazolιdιne-2-one (0 336 g, 1 mmol). and the solution kept at r t for 1 h Solvents were removed in vacuo to afford 5-(S)- azιdomethyl-3-[4'-carboxy-3 ' -fluorophenyl]oxazohdιne-2-one (0 280 g. 997c) A mixture of 5-(S)-azιdomethyl-3-[4'-carboxy-3 ' -fluorophenyl]oxazohdιne-2-one well stiπed mixture of (0 080 g. 0 286 mmol) and thiosemicarbazide (0 0957 g. 0 286 mmol) in dioxane (2 mL) was heated until the mixture was homogeneous Phosphorous oxychlonde (0 027 ml. 0 29 mmol) was added, and the mixture heated at reflux for 1 h The mixture was allowed to cool to r t . and the white precipitate filtered, washed with dioxane, suspended in saturated aqueous sodium bicarbonate, and extracted with ethyl acetate Combined oganic extracts were washed with bnne. and dned (MgS0 4 ) Solvent was removed under vacuum, and the crude product purified by PTLC ( 107o MeOH in DCM) to give product as a white solid (0 038 g. 40 7c), MS (m/z) [M+H] + = 336 5-(S)-Amιnomethyl-3-[4'-(5"-formamιdo-l".3" 4"-thιadιazole-2"-yl)-3 ' -fluoro- phenyl]oxazolιdιne-2-one 5-(S)-Azιdomethyl-3-[4'-(5"-amιno-l",3".4"-thιadιazole-2"- yl)amιnocarbonyl-3' -fluorophenyl ]oxazohdιne-2-one (0.335 g, 1 0 mmol), p- mtrophenyl formate (0.188 g, 1 12 mmol), and 2,6-di-(tert-butyl)pyndine (0 336 mL, 1 50 mmol) in THF (4 mL) is stiπed at 50-65 °C overnight Solvent is removed under vacuum, and the resulted 5-(S)-azιdomethyl-3-[4'-(5"-foπnamιdo- l".3".4"-thιadιazole-2"-yl)ammocarbonyl-3'-fluorophenyl]oxazohdιne-2-one intermediate is punfied by PTLC (MeOH - DCM) A mixture of 5-(S)- azιdomethyl-3-[4'-(5"-formamιdo-l".3".4"-thιadιazole-2"-yl)amιnocarbonyl-3 ' - fluorophenyl]oxazohdιne-2-one (0 363 g. 1 mmol) and tnphenylphosphine (0 262 g. 1 0 mmol) in THF (ca 10 mL) is stiπed at r t for 3-4 h and then at 40 °C for 2 h Water (0.5 mL) is added, and the mixture stiπed at 40°C overnight Solvents are removed in vacuo. and the crude product purified by PTLC (MeOH - DCM) 5-(S)-Acetamιdomethyl-3-[4'-(5"-formamιdo-l".3".4"-thιadιazole-2"-yl)-3 ' - fluorophenylloxazolιdme-2-one Acetic anhydride (0.14 mL. 1.5 mmol) is added to 5-(S)-amιnomethyl-3- [4'-(5"-formamιdo-l".3".4"-thιadιazole-2"-yl)-3 ' -fluoro-phenyl]oxazohdιne-2- one (0.34 g, 1 mmol) and polyvinylpyndine (0.50 g) in THF (7 mL), and the mixture is agitated at r.t. for 4 h. Supernatant is collected by filtration, and the resin washed with excess THF. Solvent is removed under vacuum to afford the product which can be further punfied by PTLC (MeOH - DCM). 5-(S)-Thιoacetamιdomethyl-3-[4'-(5"-thιoformamιdo- l".3".4"-thιadιazole-2"-yl)- 3 ' -fluorophenylloxazohdine-2-one. 5-(S)-Acetamιdomethyl-3-[4'-(5"-formamιdo-l".3".4"-thιadιazole-2"-yl)- 3'-fluoro-phenyl]oxazohdιne-2-one (0.38 g, 1.0 mmol) and Lawesson reagent (0.40 g. 1.0 mmol) in dioxane ( 10 mL) is stiπed at 50-65 °C for 4-6 h. Solvent is removed under vacuum and the residue punfied by PTLC (MeOH - DCM) Example 35 5-(S)-Azιdomethyl- 3-r4'-(5" -methylamιno-1" .3".4" -thιadιazole-2' '-γl)-3' -fluoro- phenvlloxazohdme- -2-one The compound is prepared analogously to descnbed above synthesis of 5- (S)-azιdomethyl-3-[4'-(5"-amιno-l".3".4"-thιadιazole-2"-yl)-3 ' - fluorophenyl]oxazohdιne-2-one from 5-(S)-azιdomethyl-3-[4'-carboxy-3'- fluorophenyl]oxazohdιne-2-one (0 10 g, 0.36 mmol). 4-methyl-3- thiosemicarbazide (0 038. 0.36 mmol ). and phosphorus oxychloπde ((0.033 mL. 0.36 mmol ) in dioxane (2 mL) Crude product is punfied by PTLC (MeOH - DCM). 5-( S )-Thιoacetamιdomethyl-3-14 ' -(5"-(N-methyl )thιoformamιdo- l " .3 " .4"- thιadιazole-2"-yl)-3 ' -f1uorophenyl1oxazohdιne-2-one. The compound is prepared from 5-(S)-azιdomethyl-3-[4'-(5"- methylamιno- l".3".4 " -thιadιazole-2 " -yl)-3 ' -fluorophenyl]oxazohdιne-2-one analogously to described above synthesis of 5-(S)-thιoacetamιdomethyl-3-[4'-(5"- thιoformamιdo-l".3".4"-thιadιazole-2"-yl)-3 ' -fluorophenyl]oxazohdine-2-one from 5-(S)-azιdomethyl-3-[4 ' -(5 " -amιno-l".3",4"-thιadιazole-2"-yl)-3 ' - fluorophenyl]oxazohdιne-2-one. Crude product is purified by PTLC (MeOH - DCM). Example 36 5-(S)-Azιdomethyl-3-[4 ' -(4"-methyl-5"-methylιmιno-4".5"-dιhvdro-l".3".4"- thιadιazole-2"-yl)-3 ' -fluorophenyl]oxazolidine-2-one. A mixture of 5-(S)-azidomethyl-3-[4'-(5"-methylammo-l".3".4"- thιadιazole-2"-yl)-3'-fluorophenyl]oxazohdιne-2-one (0.10 g, 0.29 mmol) and methyl iodide (0.036 mL. 0.57 mmol) in dioxane (ca. 2 mL) is stiπed under reflux overnight. Solvent is removed under vacuum, and the crude product is punfied by PTLC (MeOH - DCM). 5-(S)-Amιnomethyl-3-f4 ' -(4"-methyl-5"-methylιmιno-4".5"-dιhvdro- l".3".4"- thιadιazole-2 " -yl)-3 ' -fluorophenylloxazohdιne-2-one. A mixture of 5-(S)-azιdomethyl-3-[4'-(4"-methyl-5"-methylιmιno-4 " .5 " - dιhydro- l".3".4"-thιadιazole-2"-yl)-3 ' -fluorophenyl]oxazohdιne-2-one ( 1 0 mmol) and tnphenylphosphine (0 262 g. 1 0 mmol) in THF (ca 10 mL) is stiπed at r t for 3-4 h and then at 40 °C for 2 h Water (0 5 mL) is added, and the mixture stiπed at 40°C overnight Solvent is removed in \acuo. and the crude product purified by PTLC (MeOH - DCM) 5-(S)-Thιoacetamιdomethyl-3-[4'-(4"-methyl-5"-methyhmιno-4".5"-dιhydro- 1 " 3" 4"-thiadiazole-2"-yl)-3 ' -fluorophenvnoxazohdine-2-one 5-(S)-Amιnomethyl-3-[4'-(4"-methyl-5"-methyhmιno-4".5"-dιhydro- l".3".4"-thιadιazole-2"-yl)-3'-fluorophenyl]oxazohdιne-2-one ( 1 O mmol) and ethyl dithioacetate (0 130 ml, 1 13 mmol) with tnethylamine (0 215 ml.l 54 mmol) in DCM is stiπed at r t overnight The reaction mixture is concentrated under vacuum and the residue punfied by PTLC (MeOH - DCM) Example 37: Protocol for Assay of Antimicrobial Activity. Minimum inhibitor concentrations (MICs) were determined using the microdilution method according to National Committee for Clinical Laboratory Standards (NCCLS) procedures Compounds were suspended in DMSO at lOmg/ml and stored at -20°C The range of concentrations tested was 64-0 06 μg/ml using two-fold dilutions To prepare the inoculum, bacterial cultures were grown overnight at 35°C on agar plates and each organism was resuspended in 1 ml saline to obtain a 0 5 McFarlands density standard This was subsequently diluted 1 200 into Mueller- Hinton Broth (MHB) or Haemophilus Test Medium (HTM. for Haemophilus) providing a final inoculum size of 5 * 10 ^ cfu/ml After inoculation with the bacteπa. assay plates were incubated at 35°C for 18-24 h The MIC was defined as the lowest concentration ot compound that did not produce visible growth after incubation Gram positive and gram negative strains used included Staphylococcus aureus. Enterococcus faecium. Enterococcus faecalis, Streptococcus pneumoniae. Haemophilus influenzae. Pseudomonas aeruginosa. Escherichia coh. and E coh (acr) - an efflux pump mutant Example 38 5-(S)-Azιdomethyl-3-[4 ' -amιnocarbonyl-3'-fluorophenylloxazolιdιne- one A solution of 5-(S)-azιdomethyl-3-[4'-carboxy-3 ' -fluorophenyl- ]oxazohdιne-2-one (3 2g. 1 1.4 mmol; prepared as descnbed in Example 3). 0-(7- azabenzotπazol- l-yl)-N.N.N'.N'.-tetramethyluronιum hexafluorophosphate (6 5g, 17 lmmole) and N,N'-dnsopropylethylamιne (5.9g, 7 9ml, 45 6 mmol) in DMF ( 12 ml) was stiπed at room temperature for 20 mm Ammonium chloride (1 2g. 22.8 mmol) was added, and the reaction mixture was stiπed at r t. overnight Most of the solvent was removed under vacuum, and the residue taken up in ethyl acetate and washed twice with 3% aq. citnc acid and bnne Organic layer was dried (Na S0 4 ) and concentrated under vacuum. Crude matenal was punfied by silica gel chromatography elutmg with 15% methanol in ethyl acetate to afford a white crystalline product (2.8g. 917c). HPLC R, = 4.7. MS (m/z)- [M+H] + = 280 5-(S)-Amιnomethyl-3-r4'-amιnocarbonyl-3'-fluorophenylloxazohdιne-2- one Tnphenylphosphine (2.9 g. 1 1.0 mmol ) was added portionwise to a solution of 5-(S)-azιdomethyl-3-[4'-amιnocarbonyl-3'-fluorophenyl]oxazohdιne- 2-one (2.8g. 10.0 mmol) in THF (75 ml) under nitrogen atmosphere. The solution was stiπed at 40° C for 2 h. water (2.0 ml) added, and the reaction mixture was stiπed at 40°C overnight. Solvent was removed under vacuum, and the resulting solid was triturated with ether. Precipitated matenal was filtered, washed with ether and ethanol and dned under vacuum to afford the product as white crystals ( 1.7g. 697c). HPLC R, = 5.0 mm. MS (m/z): [M+H] + = 254. 5-(S)-Thιoacetamιdomethyl-3-r4'-amιnocarbonyl-3 ' - fluorophenyl]oxazohdιne-2-one. A solution of 5-(S)-amιnomethyl-3-[4'-amιnocarbonyl-3 ' - fluorophenyl]oxazohdιne-2-one (1.75 g, 6.9 mmol), tnethylamine (2.0 ml, 13.8 mmol) and ethyl dithioacetate (0.87 ml, 7.6 mmol) and DMF (5 ml) in acetonitnle (5 ml) was stiπed at r.t. for 48 h. Solvent was removed under vacuum, and the crude material punfied by silica gel chromatography (eluent: 10% methanol in ethyl acetate). White crystalline solid (1.3 g. 61%). HPLC R, = 4.5 mm. MS (m/z): [M+H] + = 312. Example 39 5-(S)-Azidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]- oxazohdιne-2-one. Pentafluorophenyl trifluoroacetate (2.2 ml. 12.9 mmol) was added dropwise with stimng to a solution of 5-(S)-azιdomethyl-3-[4'-carboxy-3' fluorophenyl]oxazohdιne-2-one (3 0 g. 10 7 mmol: prepared as described in Example 3) and pyndine (3.5 ml. 42.8 mmol ) m DMF ( 10 ml ). The mixture was stiπed at r.t. for 2.5 h. and ethyl acetate with 3% aq. citric acid added. Organic layer was washed twice with 37c citric acid, brine, and dried (NaιS0 4 ). The crude material was washed with ether-hexanes to afford a white crystalline product (4.3g. 907c). HPLC R, = 7 1. MS (m/z): [M+Hf = 447. 5-(S)-Azιdomethyl-3-[4 ' -(N-methoxyamιno)carbonyl-3'-fluorophenyll- oxazohdιne-2-one. N-Methoxyamine hydrochlonde ( 123 mg. 1.5 mmol) was added to a solution of 5-(S)-azιdomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3 * - fluorophenyl]-oxazohdme-2-one (600 mg. 1.3 mmol) and dnsopropylethylamine (0.26ml. 1.5 mmol) in THF (8 ml), and the mixture stiπed overnight at r.t.. Solvent was removed under vacuum, and ethyl acetate with 3% aq. citnc acid added. Organic layer was washed twice with 37c citric acid. bnne. and dried (Na 2 S0 4 ). Solvent was removed under vacuum, and the crude matenal crystallized from ethanol-ether to give a white crystalline product (335 mg, 837c). HPLC R, = 4.8. MS (m/z): [M+H] + = 310. 5-(S)-Amιnomethyl-3-[4'-(N-methoxyamιno)carbonyl-3'-fluorophenyn- oxazolidine-2-one. Tnphenylphosphine (317 mg, 1.2 mmol) was added to a solution of 5-(S)- azιdomethyl-3-[4'-(N-methoxyamιno)carbonyl-3'-fluorophenyl]-oxazohdιne-2- one. (0.335 g. 1.1 mmol) in THF (8 ml) under nitrogen atmosphere. The solution was stiπed at 40° C for 2 h. water (0.24 ml) was added, and the reaction mixture stiπed at 40° C overnight. Solvent was removed under vacuum, and the resulting solid was triturated with ether. Precipitated material was filtered, washed with ether and ethanol and dried under vacuum to afford the product as white crystals ( 120 mg, 427c). HPLC R, = 3.5 mm. MS (m/z): [M+H] + = 284. 5-(S)-Thιoacetamιdomethyl-3-[4'-(N-hydroxyamιno)carbonyl-3'- fluorophenyll-oxazohdιne-2-one. A solution of 5-(S)-amιnomethyl-3-[4'-(N-methoxyamιno)carbonyl-3 ' - fluorophenyl]-oxazohdιne-2-one (0.053 ml. 0.47 mmol), tnethylamine (0.12 ml. 0.84 mmol) and ethyl dithioacetate (0.87 ml. 7 6 mmol) in DMF (0.75 ml) was stiπed at r.t. for 48 h. Solvent was removed under vacuum, and the crude material punfied by silica gel PTLC (eluent: 5% MeOH in ethyl acetate). White crystalline solid ( 100 mg, 707c). HPLC R, = 4.6 min. MS (m/z): [M+H] + = 342. Example 40 5-(S)-Acetamιdomethyl-3- '-(N.N-dιmethylamιno)carbonyl-3 ' fluorophenvn-oxazohdme-2-one. A mixture of 5-(S)-thιoacetamιdomethyl-3-(4'-carboxy-3 ' - fluorophenyl)oxazohdιne-2-one (0.33 g. 1.06 mmol. prepared as described in Example 13 ), 0-(7-azabenzotπazol- 1 -yl )-N.N,N' .N' .-tetramethyluronium hexafluorophosphate (0.428 g. 1.1 mmole) and N.N " -dιιsopropylethylamιne (0.38 ml. 2.1 mmol) in DMF ( 1.5 ml) was stiπed at r.t. for 20 min. Dimethylamine hydrochlonde (96 mg. 1.2 mmole) was added, and the mixture stiπed at r.t. overnight. Solvent was removed under vacuum, and the product punfied by by silica gel PTLC (eluent: 107c MeOH in ethyl acetate) White crystals ( 1 17 mg, 33%). HPLC R, = 4.2. MS (m/z): [M+H] + = 340. Example 41 5-(S)-Acetamιdomethyl-3-[4 ' -(pentafluorophenoxy)carbonyl-3 ' fluorophenyl1-oxazohdine-2-one. 607c TFA in dichloroethane (10 ml) was added to 5-(S)-azιdomethyl-3-[4'- ft?rr-butoxycarbonyl-3'-fluorophenyl]oxazohdine-2-one (2.00 g. 5.95 mmol; prepared as descnbed for Example 2) and the solution kept at r.t. for 1 h. Solvent was removed under vacuum to afford 5-(S)-azidomethyl-3-[4'-carboxy-3 ' - fluorophenyl]oxazolidιne-2-one (1.65 g, 5.89 mmol. 99%). This intermediate was dissolved in DMF (15 ml), and pentafluorophenyl trifluoroacetate ( 1.21 ml. 7.06 mmol) and pyndine (1.91 ml. 23.6 mmol) were added with stiπing. The mixture was stiπed at r.t. for 3 h, most of the solvent removed under vacuum, and the residue tnturated with water. The resulting precipitate was filtered, washed with water, ether, and dned under vacuum. White crystals. Yield g (2.53 g. 937c) MS (m/z): [M+H] + = 463. 5-(S)-Acetamιdomethyl-3-f4'-(hydrazιno)carbonyl-3 ' - fluorophenyl]oxazohdιne-2-one. Hydrazme (0 041 ml. 1.30 mmol) was added dropwise with stirπng to a solution of 5-(S)-acetamιdomethyl-3-[4 ' -(pentafluorophenoxy)carbonyl-3'- fluorophenyl]oxazohdιne-2-one (0.500 g. 1 08 mmol) in tetrahydrofuran (3 ml) The mixture was stiπed at r t. for 2 h. and the heavy white precipitate filtered, washed with ether, and dried under vacuum Yield 0.295 g (887o) MS (m/z)- [M+Hf = 31 1 5-(S)-Thιoacetamιdomethyl-3-[4 ' -(hvdrazιno)carbonyl-3'- fluorophenylloxazohdine-2-one. Tetrahydrofuran (5 ml) was added to a mixture of phosphorous pentasulfide (0.143 g, 0.322 mmol) and sodium carbonate (0.0341 g, 0.322 mmol) under a nitrogen atmosphere, and the mixture stiπed vigorously at r.t until a clear yellow solution was obtained. 5-(S)-Acetamιdomethyl-3-[4'-(hydrazιno)carbonyl- 3'-fluorophenyl]oxazohdιne-one (0.100 g, 0.322 mmol) was added in one portion, and the reaction stiπed at r.t. overnight. Solvent was removed under vacuum, and the residue punfied by PTLC (10% methanol in DCM) to give the pure product as a white solid (0.037 g, 357c). M.p. 177 ° C. MS (m/z). [M+H] + = 327. Example 42 5-(S)-Acetamιdomethyl-3-l " 4'-(N-hydroxyamιdmo)-3'- fluorophenylloxazohdιne-2-one. O-Trimethylsilylhydroxylamine (0.37 ml, 3.0 mmol) and 5-(S)- acetamιdomethyl-3-[4 ' -cyano-3'-fluorophenyl]oxazohdιne-2-one (0.277 g. 1.0 mmol) m ethanol (3 0 ml) were stiπed at 80 °C in a sealed reaction vial for 2.5 h The mixture was left at r t for 48 h. and the crystallized product filtered, rinsed with ethanol (ca 0 75 ml ), washed with ether, and dried under vacuum. Yellow crystals Yield 0 260 g (847c) HPLC. R, 2.6 mm. MS (m/z): [M+H] + = 31 1 5-( S)-Thιoacetamιdomethyl-3-f4'-(N-hvdroxyamιdιno)-3 ' - fluorophenyl]oxazohdιne-2-one. The compound is made analogously to that described above for Example 42 from 5-(S)-acetamιdomethyl-3-[4'-(N-hydroxyamιdmo)-3 ' - fluorophenyl]oxazohdιne-2-one (0.100 g. 0.32 mmol). phosphorous pentasulfide (0 143 g. 0.322 mmol) and sodium carbonate (0.0341 g. 0.322 mmol). The reaction is performed at r.t. overnight. Solvent is removed under vacuum, and the product isolated by preparative reverse phase HPLC. Example 43 5-(S)-Acetamιdomethyl-3-[4 ' -(N-methoxyamιdmo)-3 ' fluorophenylloxazohdιne-2-one. Iodomethane (0.02 ml. 0.39 mmol) was added to a solution of 5-(S)- acetamιdomethyl-3-[4 ' -(N-hydroxyamιdιno)-3'-fluorophenyl]oxazohdιne-2-one (0.080 g. 0.26 mmol) and tert-butyl- 1, 1.3.3-tetramethylguanιdme (0.058 ml. 0.39 mmol) in DMF (1.0 ml), and the mixture wasstiπed at r.t. overnight. Solvent was removed under vacuum, and the crude product punfied by silica gel PTLC (10% methanol in DCM). HPLC: R, 3.6 mm. MS (m/z): [M+Hf = 325 5-(SyThιoacetamιdomethyl-3-[4'- (N-methoxyamιdιno)-3 ' - fluorophenylloxazolιdιne-2-one The compound is made analogously to that described above for Example 42 from 5-(S)-acetamιdomethyl-3-[4'-(N-methoxyamιdιno)-3 ' - fluorophenyl]oxazohdιne-2-one. phosphorous pentasulfide. and sodium carbonate in THF The reaction is performed at r.t overnight Solvent is removed under vacuum, and the product isolated by preparative reverse phase HPLC Example 44 5-(S)-Acetamιdomethyl-3-[4'-(N.N.N-tπmethylamιnιmιdo)carbonyl-3'- fluorophenyll-oxazohdιne-2-one LiH (0.008 g, 1.1 mmol) was added to a solution of 5-(S)- acetamιdomethyl-3-[4 ' -(hydrazιno)carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0 018 g, 0 058 mmol) and methyl iodide (0.062 ml. 1.0 mmol) in dry DMSO (0.50 ml), and the mixture was stiπed at r.t. overnight. The reaction was quenched with methanol (1.0 ml) and water (1.0 ml), and the product was punfied by preparative reverse phase HPLC (gradient from 100% of 0.17c aq. TFA (solvent A) to 607c 0 17c TFA in acetonitnle - 407o of solvent A over 40 min) White solid Yield 0.005 g (25%). HPLC: R t 2.9 min. MS (m/z): [M+H] + = 353 5-(S)-Thιoacetamιdomethyl-3-[4'-(N.N.N-tnmethylamιnιmιdo)carbonyl- 3'-fluorophenyn-oxazohdme-2-one The compound is made analogously to that described above for Example 42 from 5-(S)-acetamιdomethyl-3-[4 ' -(N.N.N-trιmethylamιnιmιdo)carbonyl-3 " - fluorophenyl]oxazoh-dιne-2-one. phosphorous pentasulfide and sodium carbonate in THF. The reaction is performed at r.t. overnight. Solvent is removed under vacuum, and the product isolated by preparative reverse phase HPLC. Example 45 5-(S)-Thιoacetamιdomethyl-3-[4'-(6"-methylsulfinylpyndιne-3"- yl)amιnocarbonyl-3'-fluorophenylloxazolιdιne-2-one. A solution of 5-(S)-thιoacetamιdomethyl-3-[4'- (pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazohdine-2-one (0.478 g. 1 0 mmol: prepared as described for Example 16), 3-amιno-6-methylsulfinylpyπdιne (0.156 g. 1.0 mmol), tnethylamine (0.202 g. 2.0 mmol) and 4- dimethylaminopyπdine (0.012 g, 0.1 mmol) in dry acetonitnle is agitated at 50-60 °C overnight. Volatiles are removed under vacuum, and the crude product punfied by PTLC (eluent: methanol-DCM). Example 46 5-(S)-Thιoacetamιdomethyl-3-[4'-(5"-methylsulfinylthιazole-2' yl)amιnocarbonyl-3'-fluorophenylloxazohdιne-2-one. A solution of 5-(S)-thιoacetamιdomethyl-3-[4'- (pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0.478 g, 1.0 mmol; prepared as described for Example 16). 2-ammo-5-methylsulfιnylthιazole (0 162 g 1 0 mmol) tnethylamine (0 202 g. 2 0 mmol) and 4- dimethylaminopyndine (0 012 g, 0 1 mmol) dry acetonitnle is agitated at 50-60 °C overnight Volatiles are removed under vacuum, and the product purified by PTLC (eluent methanol-DCM) Example 47 5-(S)-Thιoacetamιdomethyl-3-I4'-(5"-methylsulfinyl-l" 3" 4"-thιadιazole- 2"-yl)amιno-carbonyl-3'-fluorophenylloxazohdιne-2-one A solution of 5-(S)-thιoacetamιdomethyl-3-[4'- (pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazohdιne-2-one (0 478 g, 1 0 mmol, prepared as descπbed for Example 16), 2-amιno-5-methylsulfinylthιazole (0 163 g, 1 0 mmol), tnethylamine (0 202 g, 2 0 mmol) and 4- dimethylaminopyndine (0 012 g, 0 1 mmol) in dry acetonitnle is agitated at 50-60 °C overnight Volatiles are removed under vacuum, and the product punfied by PTLC (eluent methanol-DCM) Example 48 5-(S)-Acetamιdomethyl-3-r4'-(3"-ethoxycarbonyl)thιoureιdo-r'-yl)-3'- fluorophenvπ-oxazohdιne-2-one Ethoxycarbonyl isothiocyanate (0 50 ml, 4 1 mmol) was added to a solution of 5-(S)-acetamιdomethyl-3-[4'-amιno-3'-fluorophenyl]oxazohdιne-2- one (0 50 g. 1 87 mmol, prepared as descnbed for Example 21) in a mixture of MP and DCM ( 1 1. 7 ml) Reaction was stiπed at r t for 3h. and the solvent was removed under v acuum. The residue was triturated with excess of hexanes and then ether. Resulted precipitate was filtered, washed with ether and dried under vaccum. Yield 0 73 g (98% ). HPLC R, 4.2 mm. MS (m/z):[M+H] + = 399. 5-(S)-Thιoacetamιdomethyl-3-|4 ' -(3"-ethoxycarbonyl)thιoureιdo-l"-yl)- 3'-fluorophenvπ-oxazohdιne-2-one. A mixture of 5-(S)-acetamιdomethyl-3-[4 ' -(3"-ethoxycarbonyl)thιoureιdo- l"-yl)-3 ' -fluorophenyl]-oxazolidιne-2-one (0.200 g. 0.50 mmol) and the Lawesson ' s reagent (0.155 g. 0.38 mmol) in 1.4-dιoxane (6 ml) was stiπed at 65° C overnight. Solvent was removed under vacuum, and the crude product purified by silica gel PTLC (eluent: 107c acetone in DCM). White solid. Yield 0.124 g (607c). HPLC R, 4 7 min. MS (m z):[M+H] + = 415. Example 49 5-(S)-Acetamιdomethyl-3-r4'-(3"-ethoxycarbonyl)ureιdo-l"-yl)-3' fluorophenyl 1-oxazohdιne-2-one. Ethoxycarbonyl isocyanate (0.29 ml. 2.8 mmol) was added to a solution of 5-(S)-acetamidomethyl-3-[4'-amιno-3'-fluorophenyl]oxazolidιne-2-one (0.50 g. 1.87 mmol: prepared as described for Example 21 ) in a mixture of NMP and DCM ( 1 : 1 : 7 ml). Reaction was stiπed at r.t. for 3h. and the solvent was removed under vacuum. The residue was triturated with excess of hexanes and then ether. Resulted precipitate was filtered, washed with ether and dned under vaccum. Yield 0.65 g (91 %). HPLC R, 4 0 min. MS (m/z):[M+H] T = 383. 5-(S -Thιoacetamιdomethyl-3-| " 4'-(3"-ethoxycarbonyl )ureιdo- l"-yl)-3 " - fluorophenyll-oxazohdιne-2-one A mixture of 5-(S)-acetamιdomethyl-3-[4 ' -(3"-ethoxycarbonyl)ureιdo- l"- yl)-3 ' -fluorophenyl]oxazohdιne-2-one (0.300 g. 0 79 mmol) and the Lawesson ' s reagent (0 32. 0.79 mmol) in 1.4-dιoxane (6 ml) was stiπed at 65° C overnight Precipitated product was filtered, washed with 1.4-dιoxane. ether, and dried under vacuum White solid Yield 0.299 g (957c). HPLC R, 4.5 min. MS (m/z)-[M+H] + = 399 Example 50 5-(S)-Acetamιdomethyl-3-r4'-(3"-methoxycarbonyl)thιoureιdo-l"-yl)-3'- fluorophenyll-oxazohdιne-2-one A solution of 5-(S)-acetamιdomethyl-3-[4'-amιno-3'- fluorophenyl]oxazohdιne-2-one (0.50 g, 1.87 mmol; prepared as described for Example 21) in NMP (2 ml) was added dropwise with stirnng to a solution of methoxycarbonyl isothiocyanate (generated in situ from methyl chloroformate (0 300 ml. 3 8 mmol) and Bu 4 NCS ( 1.25 g. 4 16 mmol) in acetonitnle (8 ml), r.t . 6 h under nitrogen atmosphere), and the mixture was stiπed at r.t. overnight. Solvents were removed under vacuum, the residue dissolved in a mixture of MeOH and DCM ( 1 1. 30 ml), and stiπed with excess of the cation exchange resm ER 120 Plus overnight. Supernatant was filtered, solvents removed under vacuum. and the crude product purified by silica gel PTLC (eluent 307c acetone in DCM) Yield 0 359 g (507c) HPLC R, 3 9 min MS (m z) [M+H] + = 385 Example 51 5-(S)-Thιoacetamιdomethyl-3-[4'-(3"-methoxycarbonyl)thιoureιdo- l " -\l)- 3' -fluorophenyl l-oxazohdme-2-one A mixture of 5-(S)-acetamιdomethyl-3-[4'-(3"- methoxycarbonyl)thιoureιdo-l"-yl)-3'-fluorophenyl]oxazohdιne-2-one (0 24 g, 0.63 mmol) and the Lawesson ' s reagent (0.24, 0 60 mmol) in 1,4-dioxane (6 ml) was stiπed at 70° C overnight Solvent was removed under vacuum, and the crude product purified by silica gel PTLC (eluent: hexanes-EtOAc 1.1). Yield 0.359 g (807c). HPLC R, 4.4 mm. MS (m/z):[M+H] + = 401 Example 52 5-(S)-Acetamιdomethyl-3-[4'-(3"-methoxycarbonyl)ureιdo-l"-yl)-3 ' - fluorophenyl l-oxazohdιne-2-one. Methoxycarbonyl isocyanate (0.20 ml, 2.47 mmol) was added to a solution of 5-(S)-acetamιdomethγl-3-[4'-amιno-3'-fluorophenyl]oxazolidme-2-one (0.525 g. 1 96 mmol prepared as described for Example 21 ) in a mixture of NMP and DCM ( L I , 10 ml). Reaction was stiπed at r.t. for 4 h The precipitated product was filtered, washed with excess of hexanes and ether, and dned under vacuum White solid, yield 0.541 g (757c). HPLC R, 3.7 mm. MS (m/z):[M+H] + = 369 5-(S)-Thιoacetamιdomethyl-3-[4 ' -(3 " -methoxycarbonyl)ureιdo-l"-yl)-3 ' fluorophenyl ]-oxazohdιne-2-one. A mixture of 5-(S)-acetamιdomethyl-3-[4 ' -(3"-methoxycarbonyl)ureιdo- l"-yl)-3'-fluorophenyl]oxazohdιne-2-one (0.291 g, 0.79 mmol) and the Lawesson ' s reagent (0 32. 0.79 mmol) in 1 ,4-dioxane (6 ml) was stiπed at 70° C overnight Precipitated product was filtered, washed with 1.4-dιoxane. ether, and dried under vacuum. White solid. Yield 0.212 g (707c). HPLC R, 4.2 mm. MS (m/z)-[M+H] + = 385 Example 53 5-(S)-Azιdomethyl-3-[4'-methylthιo-3'-fluorophenyl]oxazohdιne-2-one 57e TFA and 2.57o tnisopropylsilane in DCM (4 ml) was added to 5-(S)- azιdomethyl-3-[4'-tnphenylmethylthιo-3'-fluorophenyl]oxazolιdme-2-one (0.250 g, 0.490 mmol; prepared as descnbed above for Example 6), and the mixture stiπed for 1 h at r.t. Solvent was removed under vacuum and the residue dissolved in DMF (2 ml). Iodomethane (0.046 ml, 0.735 mmol) was added followed by dropwise addition of tnethylamine (0 136 ml, 0.979 mmol). The mixture was stiπed at r.t. for 2 h, evaporated, and the residue punfied by PTLC (507c ethyl acetate in DCM) to give the product as a white solid (0.124 g. 907c) MS (m/z)- [M+H] + = 283 5-(S)-Azιdomethyl-3-f4'-methylsulfιnyl-3'-fluorophenylloxazolιdιne-2- one m-Chloroperoxybenzoic acid (777c. 0.079 g. 0 354 mmol) was added portionwise with stiπing to a solution of 5-(S)-azιdomethyl-3-[4'-methylthιo-3'- fluorophenyl]oxazohdιne-2-one (0 100 g. 0.354 mmol) in DCM (4 ml) at 0 °C The mixture was allowed to warm up to r.t. over 2h. The mixture was washed with aq. saturated sodium bicarbonate, bnne, dried (MgS0 4 ). and evaporated to give product as a white solid (0.100 g, 957c). MS (m z): [M+H] + = 299. 5-(S)-Amιnomethyl-3-[4 ' -methylsulfιnyl-3'-fluorophenyl]oxazolιdιne-2- one A mixture of tnphenylphosphine (0.092 g, 0.352 mmol) and 5-(S)- azιdomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolιdιne-2-one (0.100 g. O.335mmol) in tetrahydrofuran (2 ml) was stiπed at r.t. for 4 h. Water (0.1 ml. 5.36 mmol) was added, and the mixture heated at 40 ° C overnight. Solvent was evaporated under vacuum and the residue punfied by PTLC (107o methanol in DCM) to give product as a white solid (0.082 g, 867c). MS (m/z): [M+H] + = 273. 5-(S)-Thιoacetamιdomethyl-3-r4'-methylsulfιnyl-3'- fluorophenvHoxazolidme-2-one. Prepared analogously to the Method A of General Methods of Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones (Example 1) from 5-(S)-amιnomethyl- 3-[4 ' -methylsulfmyl-3 ' -fluorophenyl]oxazolιdιne-2-one (0.050 g, 0.184 mmol ) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0 05 g (967r). M.p 158-60 °C. MS (m/z). [M+H] + = 331. Example 54 5-( S)-Azιdomethyl-3-[4 ' -ethyl thιo-3 ' -fluorophenyl1oxazohdιne-2-one. This compound was prepared analogously to the synthesis of 5-(S)- azιdomethyl-3-[4 ' -methylthιo-3'-fluorophenyl]oxazohdιne-2-one from lodoethane (0.1 17 ml. 1.47 mmol) and 5-(S)-azιdomethyl-3-[4 ' -triphenylmethylthιo-3 " - fluorophenyl]oxazohdine-2-one (0.500 g. 0.979 mmol). Yield 0.267 g (927c). MS (m/z). [M+H] + = 297. 5-(S)-Azidomethyl-3-r4'-ethylsulfinyl-3'-fluorophenylloxazolidine-2-one. This compound was prepared analogously to the synthesis of 5-(S)- azιdomethyl-3-[4'-methylsulfmyl-3'-fluorophenyl]oxazolidine-2-one from 5-(S)- azιdomethyl-3-[4'-ethylthio-3'-fluorophenyl]oxazohdine-2-one (0.250 g, 0.844 mmol) and m-chloroperoxybenzoic acid (77%. 0.189 g. 0.844 mmol). Yield 0.235 g (897c). MS (m/z): [M+H] + = 313. 5-(S)-Aminomethyl-3-r4'-ethylsulfιnyl-3'-fluorophenylloxazolidιne-2-one. This compound was prepared analogously to the synthesis of 5-(S)- amιnomethyl-3-[4 ' -methylsulfinyl-3 ' -fluorophenyl]oxazolιdme-2-one from 5-(S)- azιdomethyl-3-[4'-ethylsulfinyl-3'-fluorophenyl]oxazohdιne-2-one (0.235 g. 0 752 mmol) and tnphenylphosphine (0 207 g. 0 790 mmol) Yield 0 177 g (827c ) MS (m/z) [M+H] + = 287 5-(S)-Thιoacetamιdomethyl-3-[4 ' -ethylsulfιnyl-3 ' - fluorophenylloxazolιdιne-2-one Prepared analogously to the Method A of General Methods of Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones (Example 1 ) from 5-(S)-amιnomethyl- 3-[4'-ethylsulfinyl-3'-fluorophenyl]oxazolιdιne-2-one (0.0885 g. 0.309 mmol) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0 104 g (987c). M p 138-9 °C MS (m/z): [M+H] + = 345 Example 55 5-(S)-Azιdomethyl-3-f4'-(2"-fluoroethyl)thιo-3 ' fluorophenvUoxazolιdιne-2-one. This compound was prepared analogously to the synthesis of 5-(S)- azιdomethyl-3-[4 ' -methylthιo-3'-fluorophenyl]oxazohdιne-2-one from 1-bromo- 2-fluoroethane (0.109 ml. 1.47 mmol) and 5-(S)-azιdomethyl-3-[4 ' - tπphenylmethylthιo-3'-fluorophenyl]-oxazohdιne-2-one (0.500 g, 0 979 mmol). Yield 0.280 g (917c). MS (m/z): [M+H] + = 315 5-(S)-Azιdomethyl-3-f4 ' -(2"-fluoroethyl)sulfmyl-3 ' - fluorophenvnoxazohdιne-2-one This compound was prepared analogously to the synthesis of 5-(S)- azιdomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolιdιne-2-one from 5-(S)- azιdomethyl-3-[4'-(2"-fluoroethyl)thio-3'-fluorophenyl]oxazolιdιne-2-one (0.280 g, 0.891 mmol) and m-chloroperoxybenzoic acid (777o, 0.200 g. 0.891 mmol). Yield 0.280 g (957c). MS (m/z): [M+H] + = 331. 5-(S)-Aminomethyl-3-I4'-(2"-fluoroethyl)sulfinyl-3'- fluorophenylloxazolidine-2-one. This compound was prepared analogously to the synthesis of 5-(S)- amιnomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazohdme-2-one from 5-(S)- azιdomethyl-3-[4'-(2"-fluoroethyl)sulfinyl-3'-fluorophenyl]oxazolidine-2-one (0.275 g, 0.833 mmol) and tnphenylphosphine (0.229 g. 0.874 mmol). Yield 0.253 g (807c). MS (m/z): [M+H] + = 305. 5-(S)-Thioacetamιdomethyl-3-[4'-(2"-fluoroethyl)sulfinyl-3 ' - fluorophenyll- oxazolidine-2-one. Prepared analogously to the Method A of General Methods of Preparation of 5-(S)-Thioamidomethyloxazolidinones (Example 1 ) from 5-(S)-amιnomethyl- 3-[4'-(2"-fluoroethyl)sulfinyl-3'-fIuorophenyl]oxazolidine-2-one (0.100 g. 0.329 mmol) and ethyl dithioacetate. Reaction was performed in DMF overnight. Yield 0.1 14 g (967c). M.p. 161 °C. MS (m/z): [M+H] + = 363 Example 56 5-(S)-Acetamιdomethyl-3-r4'-methylsulfiny]-3'-fluorophenvHoxazolidine- -one. Acetic anhydride (0 173 ml 1 83 mmol) and pyndine (0 296 ml 3 67 mmol) were added to a solution of 5-(S)-amιnomethyl-3-[4 -methylsulfinyl-3'- fluorophenyl]oxazohdιne-2-one (0 100 g 0 367 mmol) in DCM (3 ml) The reaction mixture was stiπed for 4 h at r t and then evaporated to dryness under v acuum The residue was punfied by PTLC ( 107c methanol in DCM) to give product as a white solid (0 1 15 g, 997c) M p 143-5 °C MS (m/z) [M+H] + = 315 5-(S)-Acetamιdomethyl-3-f4' -methylsulfonyl-3 ' - fluorophenylloxazohdιne-2-one m-Chloroperoxybenzoic acid (77%, 0 0784 g. 0 350 mmol) was added portionwise to a solution of 5-(S)-Acetamιdomethyl-3-[4'-methylsulfinyl-3 - fluorophenyl]oxazohdme-2-one (0 110 g. 0 350 mmol) in DCM (20 ml) at r t The mixture was stiπed for 2h, then washed with aq saturated sodium bicarbonate, brine, dned (MgS0 4 ). and evaporated to give product as a white solid (0 106 g, 927c) MS (m/z) [M+H] + = 331 5-(S)-Thιoamιdomethyl-3-r4' -methylsulfonyl-3 ' - fluorophenynoxazohdιne-2-one Prepared analogously to the Method B (Example 1) of General Methods for Preparation of 5-(S)-Thιoamιdomethyloxazohdιnones from 5-(S)- acetamιdomethyl-3[4 -methylsulfonyl-3'-fluorophenyl]oxazohdιnone (0 100 g. 0 303 mmol) and Lawesson s reagent Yield 0 078 g (757c) M p 177 °C MS ( m/z) [M+H] + = 347 Example 57 5-(S)-Amιnomethyl-3-(4 ' -(5"-amιno-l" 3".4"-thιadιazole-2"-yl)-3 ' - fluorophenyll-oxazohdιne-2-one Tnphenylphosphine (0 376 g. 1 4 mmol) was added to a mixture of 5-(S)- azιdomethyl-3-[4'-(5"-amιno-l".3",4"-thιadιazole-2"-yl)-3 ' - fluorophenyl]oxazohdιne-2-one (0 402 g, 1 3 mmol, prepared as descπbed for Example 34) in DMF (7 ml) under nitrogen atmosphere The solution was stiπed at 40° C for 6 h, then water (0 7 ml) was added, and the reaction mixture stiπed at 55° C overnight Most of solvent was removed under vacuum, and the resulting solid was triturated with ether Precipitated matenal was filtered, washed with MeOH, excess of ether, and dned under vacuum to afford the product as a white solid (0 320 g, 807c) MS (m/z) [M+H] + = 310 5-(S)-Thιoacetamιdomethyl-3-r4 , -(5"-amιno-r',3".4"-thιadιazole-2"- yl)fluorophenyll-oxazolιdιne-2-one A solution of 5-(S)-amιnomethyl-3-[4'-(5"-amιno-l",3",4"-thιadιazole-2"- yl)-3'-fluorophenyl]oxazohdιne-2-one (0 155 g, 0 5 mmol) and ehyl dithioacetate (0 093 ml. 0 67 mmol) with tnethylamine (0 080 ml, 0 67 mmol) in DMF (2 ml ) was stiπed at r t overnight Most of the solvent was removed under vacuum, residue washed with ether, and the crude product punfied by silica gel PTLC (eluent 107c MeOH in DCM) White crystals, yield 0 92 g (507c) HPLC R,= 3 8 mm MS (m/z) [M+H] + = 368 Example 58 5-(S)-Azιdomethyl-3-[4' -(thiosemicarbazide- l"-yl)carbonyl-3' - fluorophenyll-oxazolιdιne-2-one A solution of 5-(S)-azιdomethyl-3-[4'-carboxy-3'- fluorophenyl]oxazohdιne-2-one ( 1.0 g, 3.6 mmol; prepared as descπbed in Example 3), 0-(7-azabenzotπazol- l-yl)-N,N,N',N',-tetramethyluronιum hexafluorophosphate ( 1.5 g, 3 9 mmol) and N,N'-dusopropylethylamιne (1 9 ml, 10.8 mmol) in DMF (4 ml) was stiπed at r.t. for 20 minutes. Thiosemicarbazide (0.351 g, 3.9 mmol) was added, and the reaction mixture was stiπed at r.t. overnight. Most of the solvent was removed under vacuum, and the crude matenal punfied by silica gel chromatography eluting with 20% hexanes in ethyl acetate to afford the white crystalline product (0.460 g, 367c). HPLC R, = 3.4 MS (m/z): [M+H] + = 354. 5-(S)-Amιnomethyl-3-[4 ' -(thiosemicarbazide- l " -yl)carbonyl-3 ' fluorophenyll-oxazolidιne-2-one. Tnphenylphosphine (0.376 g, 1.4 mmol) was added to a solution of 5-(S)- azidomethyl-3-[4' -(thiosemicarbazide- l-yl)carbonyl-3'-fluorophenyl]- oxazolidme-2-one (0.46 g. 1.3 mmol) in THF (15 ml) under nitrogen atmosphere. The solution was stiπed at 40° C for 3 h. water (1.5 ml) was added, and the reaction mixture stiπed at 40° C overnight. Solvent was removed under vacuum, and the resulting solid was triturated with ether. Precipitated material was filtered, washed with ether and ethanol and dried under vacuum to afford the product as white crystals (0.370 g, 877c). HPLC R, = 3.2 min. MS (m/z): [M+H] + = 328. 5-(S)-(tert-Butoxycarbonyl)aminomethyl-3-r4' -(thiosemicarbazide- 1"- yl)carbonyl-3'-fluorophenyll-oxazolidine-2-one. di-tert-Butyl dicarbonate (0.288 g, 1.3 mmol) was added with stirring at 5 °C to the mixture of 5-(S)-aminomethyl-3-[4' -(thiosemicarbazide- l-yl)carbonyl- 3'-fluorophenyl]-oxazolidine-2-one (0.370 g, 1.1 mmol) and triethylamine (0.31 ml. 2.2 mmol) in THF (30 ml) with DMF (5 ml). The mixture was stiπed overnight at r.t.. and solvent was removed under vacuum. The residue was partitioned between EtOAc and water, and resulted emulsion filtered through Cehte. Organic layer was separated and dried (Na 2 S0 4 ). Evaporation of solvent afforded a white crystalline product (0.480 g, quant.). HPLC R, = 4.3 mm. MS (m/z): [M+H] + = 428. 5-(S)-(tert-Butoxycarbonyl)ammomethyl-3-[4'-(5"-amιno-l".3".4"- oxadιazole-2"-yl)-3 ' -fluorophenyl]-oxazolιdιne-2-one A mixture of 5-(S)-(tert-butoxycarbonyl)amιnomethyl-3-[4'- (thiosemicarbazide- 1 "-yl )carbonyl-3 ' -fluoropheny l]-oxazohdme-2-one (0.425 g, 1 0 mmol) and red mercury (II) oxide (0.432 g, 2.0 mmol) in DMF (3 ml) was stiπed at 60° C for 2 h. Solvent was removed under vacuum, and the crude matenal punfied by silica gel chromatography (eluent: EtOAc) to afford a white crystalline product (0.160 g, 417c). HPLC R t + 4.5 mm. MS (m/z): [M+H] + = 394. 5-(S)-Thιoacetamιdomethyl-3-r4'-(5"-amιno-l".3".4"-oxadιazole-2"-yl)- 3'-fluorophenyll-oxazolιdιne-2-one. A solution of 5-(S)-(tert-butoxycarbonyl)ammomethyl-3-[4'-(5"-amιno- l",3",4"-oxadιazole-2"-yl)fluorophenyl]-oxazohdιne-2-one. (0.160 g, 0.41 mmol) in 40% tnfluoroacetic acid in DCM (8 ml) was stiπed at r.t. for 1.5 h. Volatiles were removed under vacuum at r.t., and the gummy residue redissolved in MeOH and evaporated to afford the intermediate 5-(S)-ammomethyl-3-[4'-(5"-amιno- l".3".4"-oxadiazole-2"-yl)fluorophenyl]-oxazohdme-2-one tnfluoroacetate as a white crystalline solid (HPLC R t = 3.1 mm. MS (m/z)- [M+H] + = 294) A solution of above intermediate and ehyl dithioacetate (0.093 ml. 0 67 mmol) with tnethylamine (0.080 ml. 0 67 mmol) in DMF (2 ml ) was stiπed at r.t. for 3 h Solvent was removed under vacuum, and the product was purified by silica gel column chromatography (eluted with a mixture of 1% AcOH and 15%> MeOH in DCM) White crystals (0 05 lg, 367c) HPLC R,= 4 0 min MS (m/z) [M+H] + = 352 Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity and understanding, it will be apparent to those skilled in the art that certain changes and modifications may be practical Therefore the descπption and examples should not be construed as limiting the scope ot the invention

Claims: CLAIMS What is claimed is: 1 A compound of formula 1 : 1 wherein: Rό is thioacyl. aminocarbonyl. alkoxycarbonyl. aminothiocarbonyl. alkoxythiocarbonyl, alkylthιo(carbonyl), or alkylthιo(thιocarbonyl); R7 is aryl or heteroaryl; R 8 is C 1 -C7 alkyl, C C 7 alkenyl. C,-C 7 alkynyl. NR, O. S. C(=0)NR. NRC(=0), C(=0). C(=O)O, OC(=0), OC(=0)NR, NRC(=0)0. C(=S)NR, NRC(=S). C(=S). C(=S)0. OC(=S), OC(=S)NR, NRC(=S)0, S(=0). SO ; , SO : NR. NRSO : . NRCONR', NRC(=S)NR', or (CH 2 ) π O. wherein n = 0-6. and wherein R and R' are independently H. alkyl, heteroalkyl. aryl or heteroaryl; and Ro is hydrogen. OH, OR". SR". NR"R'", alkyl. aryl, heteroalkyl. or heteroaryl. and wherein R" and R' " are independently H. alkyl, heteroalkyl. aryl or heteroaryl. 2. The compound of claim 1 wherein: R 8 is NR. S. C(=0)NR. NRC(=0). C(=0)0, OC(=0). OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR, NRC(=S)0, or NRC(=S)NR', wherein R and R' are independently H. alkyl, heteroalkyl. aryl or heteroaryl; and Rq is hydrogen. OR". SR". NR"R' ". alkyl. aryl, or heteroaryl. wherein each R " and R' " are independently H, alkyl. aryl or heteroaryl. 3 The compound of claim 1 wherein R & is a thioacyl group. 4. A compound of claim 3 wherein the thioacyl group is selected from the group consisting of C(=S)CH C(=S)CH : CH 1 . C(=S)H. and C(=S) cyclopropyl. 5. A compound of formula 3. wherein: R 7 is aryl or heteroaryl; R 8 is C 1 -C7 alkyl, C 1 -C 7 alkenyl, Cj-C 7 alkynyl, NR, O, S, C(=0)NR. NRC(=O), C(=O). C(=0)0, OC(=O), OC(=0)NR, NRC(=0)0, C(=S)NR. NRC(=S), C(=S), C(=S)O, OC(=S), OC(=S)NR. NRC(=S)0. S(=0). SO 2 , S0 2 NR. NRSO 2 . NRCONR'. NRC(=S)NR'. or (CH : ) n O. wherein n = 0-6. and wherein each R and R' are independently H. alkyl, heteroalkyl. aryl or heteroaryl: R 9 is hydrogen, OH. OR". SR". NR"R" \ alkyl. aryl. heteroalkyl. or heteroaryl, and wherein each R" and R'" are independently H. alkyl. heteroalkyl, aryl or heteroaryl; and Rio IS H. alkyl, heteroalkyl, aryl or heteroaryl. 6. The compound of claim 5 wherein R J O is H; Cj- 4 alkyl, optionally substituted with one or more of F. CI. CN, N0 2 . and COOC alkyl. 7. The compound of claim 5. wherein: R 8 is NR. S. C(=0)NR. NRC(=0). C(=0)0. OC(=0), OC(=0)NR, C(=S)NR. NRC(=S), OC(=S)NR, NRC(=S)0. or NRC(=S)NR'. wherein R and R' are independently H, alkyl, heteroalkyl, aryl or heteroaryl; and RQ is hydrogen, OR" . SR", NR"R'", alkyl, aryl, or heteroaryl, wherein R" and R' " are independently H, alkyl, aryl or heteroaryl. 8. A compound of formula 4: wherein: R7 is aryl or heteroaryl; R 8 is NR, S, C(=0)NR, NRC(=0), C(=0)0, OC(=0), OC(=0)NR. C(=S)NR. NRC(=S), OC(=S)NR, NRC(=S)0. or NRC(=S)NR', wherein R and R' are independently H, alkyl. heteroalkyl, aryl or heteroaryl; and RQ is hydrogen, OR", SR", NR"R'", alkyl, aryl, or heteroaryl, wherein R" and R'" each are independently H, alkyl, heteralkyl, aryl or heteroaryl; and Rio and Ru are independently hydrogen, alkyl, heteroalkyl. aryl or heteroaryl, or NRj 0 Rιι is NH 2 , NHC,- 4 alkyl, N(Cj-C 4 alkyl) 2 , or N(CH 2 ) 2 . 5 . A compound of formula 5 wherein R7 is aryl or heteroaryl. R 8 is NR. S, C(=0)NR. NRC(=0), C(=0)0. OC(=0), OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR. NRC(=S)0. or NRC(=S)NR'. wherein R and R ' are independently H. alkyl, heteroalkyl. aryl or heteroaryl, and Rg is hydrogen, OR". SR", NR"R' ". alkyl. aryl, or heteroaryl. wherein R" and R' " each are independently H. alkyl, heteroalkyl, aryl or heteroaryl, and Rio IS alkyl, Cj-C 4 alkyl. heteroalkyl. aryl or heteroaryl 10 A compound of formula 6 wherein. R7 is aryl or heteroaryl, R 8 is C 1 -C7 alkyl, Cj-C 7 alkenyl, C,-C 7 alkynyl, NR. O. S. C(=0)NR. NRC(=0). C(=O). C(=0)0. OC(=0). OC(=0)NR. NRC(=0)0, C(=S)NR. NRC(=S), C(=S), C(=S)0, OC(=S), OC(=S)NR. NRC(=S)0. S(=O). S0 2 . S0 NR, NRSO 2 , NRCONR' . NRC(=S)NR' . or (CH 2 ) n O. wherein n = 0-6, and wherein R and R' are independently H. alkyl, heteroalkyl, aryl or heteroaryl; RQ is hydrogen. OH. OR". SR", NR"R'". alkyl. aryl, heteroalkyl. or heteroaryl. and wherein R" and R' " are independently H. alkyl. heteroalkyl, aryl or heteroaryl; Rio and Rn are independently hydrogen, alkyl. heteroalkyl. aryl or heteroaryl. and optionally NRj 0 Rn is NH 2 , NHCj- 4 alkyl. N(Cι-C 4 alkyl) 2 , or N(CH 2 ) 2 - 5 . 1 1. The compound of claim 10. wherein. Rg is NR. S. C(=0)NR. NRC(=0). C(=0)0. OC(=O), OC(=0)NR. C(=S)NR. NRC(=S). OC(=S)NR. NRC(=S)0. or NRC(=S)NR\ wherein R and R' are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and Ro is hydrogen, OR", SR", NR"R' ". alkyl, aryl. or heteroaryl, wherein R " and R ' " are independently H. alkyl. aryl or heteroaryl 12. A compound of formula 7: wherein: R 7 is aryl or heteroaryl; Rg is Cj-C 7 alkyl, C,-C 7 alkenyl, C,-C 7 alkynyl, NR. O. S, C(=0)NR. NRC(=0). C(=O), C(=0)0. OC(=0), OC(=0)NR, NRC(=0)0, C(=S)NR. NRC(=S), C(=S), C(=S)0. OC(=S), OC(=S)NR, NRC(=S)0. S(=0). S0 2 , S0 2 NR. NRS0 2 , NRCONR', NRC(=S)NR'. or (CH 2 ) n O, wherein n = 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl, aryl or heteroaryl; R 9 is hydrogen. OH. OR", SR", NR"R"\ alkyl, aryl, heteroalkyl. or heteroaryl, and wherein R" and R'" are independently H, alkyl, heteroalkyl. aryl or heteroaryl; and Rio is alkyl, Cj-C 4 alkyl, heteroalkyl, aryl or heteroaryl. 13. The compound of claim 12, wherein: R 8 is NR, S. C(=0)NR, NRC(=0), C(=0)0, OC(=0), OC(=0)NR. C(=S)NR. NRC(=S), OC(=S)NR, NRC(=S)0, or NRC(=S)NR', wherein R and R' are independently H, alkyl, heteroalkyl, aryl or heteroaryl; and RQ is hydrogen, OR". SR", NR"R'", alkyl. aryl, or heteroaryl. wherein R" and R ' " are independently H, alkyl, aryl or heteroaryl. 14 A compound of the structure lb 1b wherein R 2 and R 4 are, independently, hydrogen, alkyl, heteroalkyl, heteroaryl or an electron withdrawing group, R ό is thioacyl, aminocarbonyl, alkoxycarbonyl, aminothiocarbonyl. alkoxythiocarbonyl, alkylthιo(carbonyl), or alkylthιo(thιocarbonyl), and C(0)NR 7 R 8 , C(S)NR 7 R 8 OC(0)NR 7 R 8 , OC(S)NR 7 R 8 , NR 7 C(0)N R 8 Ro. NR 7 C(S)N RgR 9 , wherein R 7 , R 8 , and R 9 are, independently, hydrogen, alkyl, heteroalkyl, aryl or heteroaryl; C(0)OR J O , wherein Rj 0 is hydrogen, alkyl, heteroalkyl, aryl or heteroaryl, C(0)Rj j, wherein Ru is hydrogen, alkyl. heteroalkyl. aryl or heteroaryl, SR, 2 , S(0) 2 R I2 , or S(0)Rj 2 , wherein R !2 is hydrogen, alkyl, heteroalkyl, aryl or heteroaryl, NR 13 R 14 wherein R ] 3 and R )4 are, independently, hydrogen, acyl. sulfonyl, alkyl. heteroalkyl. aryl or heteroaryl. 2-oxazolyl compπsing R 1 at the 4-posιtιon and RJ O at the 5- position of the oxazolyl, wherein and Rj 6 are, independently, hydrogen, alkyl. heteroalkyl. aryl, heteroaryl or an electron withdrawing group, 2-amιnotfπazolyl comprising R]7 at the 4-posιtιon and R 18 at the 5- position of the thiazole. wherein R17 and R|8. are. independently, hydrogen, alkyl. heteroalkyl. aryl. heteroaryl or an electron withdrawing group. and CH2NR10R20, wherein Rj and R 2 o are. independently, hydrogen, alkyl. heteroalkyl. aryl, heteroaryl. acyl or sulfonyl. 2-(l,3.4-thιadιazolyl) comprising R 1 at the 5-posιtιon of the 1.3,4- thiadiazole. wherein R 2 j is hydrogen, alkyl, heteroalkyl. amιno(Cι_ 4 alkyl), acylamιno(Cι_; alkyl), thιoacylamιno(Cι-4 alkyl), sulfonamido(Cj_4 alkyl), heterocarbonylamιno(Cj_ 4 alkyl), aryl, heteroaryl, an electron withdrawing group, or NR 22 R 3 , wherein R 22 and R 23 are, independently, hydrogen, acyl, thioacyl, sulfonyl, alkyl, heteroalkyl, aryl or heteroaryl, CH=CHR 2 or CtR^, wherein R 24 is C(0)NR 7 R 8 , C(S)NR 7 R 8 OC(0)NR 7 Rg, OC(S)NR 7 Rg, NR 7 C(0)N R 8 R 9 , NR 7 C(S)N R 8 R 9 , C(O)OR 10 , C(0)Rj ι, SR, 2 , S(0) 2 Rj 2 , S(0)R 12 , NR, 3 Rι 4 , CH2NR, 9 R o, alkyl. aryl, or heteroaryl; or 5.6-dιhydro-l,4,2-dιoxazιne-3-yl, wherein R7 5 is at the 5-posιtιon of dioxazine, and R 26 is at the 6-posιtιon of dioxazine. and wherein R25 and R 26 , are, independently, hydrogen, alkyl. heteroalkyl, aryl, heteroaryl or an electron withdrawing group; wherein optionally R\ and R 2 together are a quinolone heterocycle C(=0)C(COOH)=CHNR 27 , or Rj and R together are a benzotnazole heterocycle NNNR 27 . or NN(R 27 )N, wherein R 27 is alkyl, aryl. or heteroaryl 15 A compound of claim 14. wherein R, is C(0)NR 7 Rg. SR π . C(S)NR7R 8 . C(O)OR 10 . C(0)Rj j. SR, : , S(0) : R, 2 , S(0)R ι: or NR n R !4 16 A compound according to claim 14. wherein Rj is C(0 NR7R 8 17 A compound according to claim 14. wherein Rj is C(0)ORJO 18 A compound according to claim 14. wherein Rj is C(0)Ru 19 A compound according to claim 14, wherein Rj is SRJO 20 A compound according to claim 14. wherein R \ is NR x (C=0)R v , wherein R and R y are independently hydrogen, alkyl, heteroalkyl, aryl, or heteroaryl 21 A compound according to claim 14. wherein Rj is NR (Sθ2)R v . wherein R and R y are independently hydrogen, alkyl, heteroalkyl, aryl. or heteroaryl with the proviso that R v is not H 22 A compound according to claim 14, wherein Rj is NRj 3 Rj4 23 A compound according to claim 14, whereir Rj is 2-oxazolyl. wherein Rj 5 is at the 4-posιtιon and Rj is at the 5-posιtιon of the oxazole group 24 A compound according to claim 14, wherein Rj is 2- ammothiazolyl. wherein R 17 is at the 4-posιtιon and Rjg is at the 5-posιtιon of the ammothiazolyl group. 25 A compound according to claim 14, wherein R\ is CH 2 NR] 9 R 2 o- 26 A compound according to claim 15, wherein R 4 is hydrogen 27 A compound according to claim 26. wherein R 2 is fluorine 28 A compound according to claim 27. wherein. R & is C(S)Cj - alkyl or C(S ) & cycloalkyl 29 A compound according to claim 28. wherein Rj is C(0)NR-Rg and R7 is hydrogen 30 A compound according to claim 29, wherein R 8 is heteroaryl 31 A compound according to claim 16, wherein R 4 is hydrogen 32 A compound according to claim 31. wherein R 2 is fluorine 33 A compound according to claim 32. wherein R is C(S)CHι. and NR 7 R 8 is NH(5 ' -(5-amιnopyπdιne-2-yl)thιopyπdιne-3 ' -yl) or NH(pyπdιne-3-yl) or NH(5-chloropyπdme-3-yl) ?4 The compound of claim 1 selected from the group consisting ot 35 The compound of claim 1 wherein the compound is 10 36 The compound of claim 1 selected from the group consisting of 15 37 The compound of claim 1 selected from the group consisting ot 38 A compound of formula 3c 3 c wherein R 2 and R4 are. independently, hydrogen, alkyl. heteroalkyl. heteroaryl or an electron withdrawing group. R 6 is thioacyl, aminocarbonyl, alkoxycarbonyl, aminothiocarbonyl, alkoxythiocarbonyl, alkylthιo(carbonyl), or alkylthιo(thιocarbonyl), R 8 is C1-C7 alkyl, C C 7 alkenyl, C,-C 7 alkynyl, NR, O, S, C(=0)NR, C(=S)NR. NRC(=0). NRC(=S), C(=0). C(=0)0, C(=S)0, OC(=0). OC(=S). S(=0). S0 2 , S0 2 NR, NRSO 2 , NRCONR', NRCSNR'. or (CH 2 ) n O. wherein n = 0-6. and wherein R and R' are independently H. alkyl. heteroalkyl, aryl or heteroaryl, and R 9 is hydrogen. OH. OR", SR", NR"R' ". alkyl. aryl, heteroalkyl. or heteroaryl. and wherein R" and R'" are independently H. alkyl, heteroalkyl. aryl or heteroaryl 39 The compound of claim 38. wherein R 6 is C(S)Cι. 7 alkyl or C(S)Cv ό cycloalkyl, R 7 is aryl; R is alkyl or heteroalkyl. 40. The compound of claim 38. wherein R 6 is C(S)C]. 7 alkyl or C(S)C 6 cycloalkyl; R 7 is aryl; R is alkvl. 41 The compound of claim 38, wherein. R 6 is C(S)C,.7 alkyl or C(S)C . 6 cycloalkyl; R7 is aryl; RQ IS alkyl. 42. The compound of claim 38, wherein the compound is selected from the group consisting of 43 The compound of claim 38. herein the compound is 44 The compound of claim 38 selected from the group consisting of 10 45 The compound of claim 38 selected from the group consisting of 46 The compound of claim 38. wherein the compound is 47 The compound of claim 38 selected from the group consisting of 10 48 The compound of claim 38 selected from the group consisting of 49 The compound of claim 38 selected from the group consisting of 50. The compound of claim 38 selected from the group consisting of 51 The compound of claim 38. wherein the compound is 52. The compound of claim 38 selected from the group consisting of 53 Λ compound of formula 4c: wherein: Rύ is thioacyl. aminocarbonyl. alkoxycarbonyl. aminothiocarbonyl. alkoxythiocarbonyl. alkylthιo(carbonyl). or alkylthiol thiocarbonyl ). Hetj is heteroaryl; Rs is C1-C7 alkyl. C,-C 7 alkenyl. C -j alkynyl. NR. O. S. C(=0)NR. C(=S)NR. NRC(=0). NRC(=S). C(=0). C(=0)0. C(=S)0. 0C(=0). OC(=S). S(=0). SO : . S0 2 NR, NRSO : . NRCONR'. NRCSNR' . or (CH 2 ) n O, wherein n = 0- 6. and wherein R and R ' are independently H. alkyl. heteroalkyl. aryl or heteroaryl; and Ro is hydrogen. OH. OR" . SR" . NR"R' " . alkyl. aryl. heteroalkyl. or heteroaryl. and wherein R " and R' " are independently H. alkyl. heteroalkyl. aryl or heteroaryl. wherein R 2 and R 4 are. independently, hydrogen, alkyl. heteroalkyl, heteroaryl or an electron withdrawing group; R is thioacyl. aminocarbonyl. alkoxycarbonyl. aminothiocarbonyl, alkoxythiocarbonyl, alkylthιo(carbonyl). or alkylthιo(thιocarbonyl); Rg is C 1 -C7 alkyl. C 1 -C7 alkenyl. C,-C 7 alkynyl, NR. O. S. C(=O)NR. C(=S)NR. NRC(=0). NRC(=S). C(=0), C(=0)0. C(=S)0, OC(=0). OC(=S), S(=0). S0 2 . SO NR. NRS0 2 . NRCONR'. NRCSNR ' , or (CH 2 ) n O. wherein n = 0- 6. and wherein R and R' are independently H, alkyl, heteroalkyl, aryl or heteroaryl; and Het 2 is a heterocyclic group. 55 The compound of claim 54. wherein R 6 is C(S)Cj. 7 alkyl or C(S)C 3 . 6 cycloalkyl. R7 is aryl, R 8 ιs S. and Het 2 is a thienylphenyl or thiazolyl group 56 The compound of claim 34. wherein R 6 is C(S)Cι - alkyl or C(S)Cι 6 cycloalkyl. R7 is aryl. Heb is 1.3.5-tπazιnvl 57 The compound of claim 54 having the structure 58 A compound of claim 1 having the structure 59 A composition for the treatment or prevention of an infectious disorder comprising an effective amount of a compound of claim 1 and a phaπnaceutically acceptable earner 60 The composition of claim 59 wherein the compound is 61 The composition of claim 59 wherein the compound is 62. The composition of claim 59 wherein the compound is 63. The composition of claim 59 wherein the compound is 64. The composition of claim 59 wherein the compound is 65 The composition of claim 59 wherein the compound is (WTw H Me 66 The composition of claim 59 w herein the compound is 67 The composition of claim 59 wherein the compound is 68. The composition of claim 59 wherein the compound is 69. The composition of claim 59 wherein the compound is 121 0. The composition of claim 59 wherein the compound is 71 The composition of claim 59 wherein the compound is selected from the group consisting of 72. A composition for the treatment or prevention of an infectious disorder compπsing an effective amount of a compound of claim 5 and a pharmaceutically acceptable earner 73 A composition for the treatment or prevention of an infectious disorder comprising an effective amount of a compound of claim 10 and a phaπnaceutically acceptable caπier 74 A composition for the treatment or prevention of an infectious disorder comprising an effective amount of a compound of claim 12 and a pharmaceutically acceptable caπier 75 A composition for the treatment or prevention of an infectious disorder compnsing an effective amount of a compound of claim 14 and a pharmaceutically acceptable earner 76 A composition for the treatment or prevention of an infectious disorder comprising an effective amount of a compound of claim 38 and a pharmaceutically acceptable earner 77 A method of treating or preventing an infectious disorder in a human or other animal subject, compnsing administering to the subject an effective amount of a compound of claim 1 78 A method of treating or preventing an infectious disorder in a human or other animal subject, compnsing admimstenng to the subject an effective amount of a compound of claim 5 79 A method of treating or preventing an infectious disorder in a human or other animal subject, compnsing admimstenng to the subject an effective amount of a compound of claim 10 80 A method of treating or preventing an infectious disorder in a human or other animal subject, compnsing admimstenng to the subject an effective amount of a compound of claim 12 81 A method ot treating or preventing an infectious disorder in a human or other animal subject, comprising administering to the subject an effective amount of a compound of claim 14 82 A method of treating or preventing an infectious disorder in a human or other animal subject, comprising administering to the subject an effective amount of a compound of claim 38 83 A method for a solid phase synthesis of the compounds of claim 5 comprising the treatment of an amide precursor comprising a group NC(0)Rjo. immobilized on a support, wherein R JO is alkyl. heteroalkyl. aryl or heteroaryl, with a thionation reagent; and release of a compound of formula 3 from the support.

Inventors: GADWOOD ROBERT C, GORDEEV MIKHAIL F, LUEHR GARY W, PATEL DINESH V, GADWOOD, ROBERT, C., GORDEEV, MIKHAIL, F., LUEHR, GARY, W., PATEL, DINESH, V.
Applicants: GADWOOD ROBERT C, GORDEEV MIKHAIL F, LUEHR GARY W, PATEL DINESH V, UPJOHN CO, GADWOOD, ROBERT, C., GORDEEV, MIKHAIL, F., LUEHR, GARY, W., PATEL, DINESH, V., PHARMACIA & UPJOHN COMPANY
Application year: 2000
Main classification: C07D263
IPC codes: A61K31, A61P31, C07D263, C07D413, C07D417