Patent ID: 6740754
Filing Date: 2004-05-25
Classification: C07B,C07C,C07D

Abstract:
A process for the production of an (S)-oxazolidinone-CH2â€”NHâ€”COâ€”RN of formula (X)Roxaâ€”RINGâ€”CH2â€”NHâ€”COâ€”RNâ€ƒâ€ƒ(X) where: RING means (I) RN is C1-C5 alkyl; (II) Roxa is phenyl substituted with one â€”F and one substituted amino group; which comprises: (1) contacting a carbamate of formula (IX) Roxaâ€”NHâ€”COâ€”Oâ€”CH2â€”X1â€ƒâ€ƒ(IX) where:(1) X1 is: (A) C1-C20 alkyl, (B) C3-C7 cycloalkyl, (C) &phgr;â€” optionally substituted with one or two: (1) C1-C3 alkyl, (2) Fâ€”, Clâ€”, Brâ€”, Iâ€”, (D) CH2&boxH;CHâ€”CH2â€”, (E) CH3â€”CH&boxH;CHâ€”CH2â€”, (F) (CH3)2C&boxH;CHâ€”CH2â€”, (G) CH2&boxH;CHâ€”, (H) &phgr;â€”CH&boxH;CHâ€”CH2â€”, (I) &phgr;â€”CH2â€” optionally substituted on &phgr;â€” with one or two â€”Cl, C1-C4 alkyl, â€”NO2, â€”CN, â€”CF3, (J) 9-fluorenylmethyl, (K) (Cl)3Câ€”CH2â€”, (L) 2-trimethylsilylethyl, (M) &phgr;â€”CH2â€”CH2â€”, (N) 1-adamantyl, (O) (&phgr;)2CHâ€”, (P) CHâ‰¡Câ€”C(CH3)2â€”(Q) 2-furanylmethyl, (R) isobornyl, (S) â€”H; (II) Roxa is as defined above; with an oxygenated amino reagent selected from the group consisting of: (1) an (S)-secondary alcohol of the formula (VIIIA) X2â€”CH2â€”C*H(OH)â€”CH2â€”NHâ€”COâ€”RNâ€ƒâ€ƒ(VIIIA) where:(I) X2 is: (A) â€”Cl, (B) â€”Br, (C) p-CH3â€”&phgr;â€”SO2â€”, (D) m-NO2â€”&phgr;â€”SO2â€”; (II) RN is as defined above; or an (S)-epoxide of the formula (VIIIB)â€”O#â€”CH2â€”C*#Hâ€”CH2â€”NHâ€”COâ€”RNâ€ƒâ€ƒ(VIIIB) where:(I) # indicates that the atoms marked with a (#) are bonded to each other resulting in the formation of a ring; (II) RN is as defined above; or an (S)-ester of the formula (VIIIC)X2â€”CH2â€”C*H(Oâ€”COâ€”RN)â€”CH2â€”NHâ€”COâ€”RNâ€ƒâ€ƒ(VIIIC) where:(I) RN and X2 are as defined above; in the presence of a lithium cation and a base whose conjugate acid has a pKa of greater than about 8.