Patent ID: 6031101
Filing Date: 2000-02-29
Classification: C07D

Abstract:
A process for preparing a compound of Formula I: ##STR35## wherein: ##STR36## represents: a) 5- or 6-membered heterocyclyl containing one, two or three double bonds, but at least one double bond and 1, 2 or 3 heteroatoms selected from O, N and S, the heterocyclyl is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3,b) 5- or 6-membered carbocyclyl containing one or two double bonds, but at least one double bond, the carbocyclyl is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3,c) aryl, wherein aryl is as defined below,C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, are unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3 ;aryl is defined as phenyl or naphthyl, which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3 or when aryl is substituted on adjacent carbons they can form a 5- or 6-membered fused ring having one, two or three heteroatoms selected from O, N, and S, this ring is unsubstituted or substituted on carbon or nitrogen with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3 ;R.sup.2 is: OR.sup.4 or N(R.sup.5).sub.2 ;R.sup.3 is:a) H,b) C.sub.1 -C.sub.8 alkyl,c) C.sub.2 -C.sub.8 alkynyl,d) C.sub.1 -C.sub.8 alkoxyl,e) C.sub.3 -C.sub.7 cycloalkyl,f) S(O).sub.t R.sup.5,g) Br, Cl, F, I,h) aryl,i) heteroaryl,j) --CHO,k) --CO--C.sub.1 -C.sub.8 alkyl,l) --CO--aryl,m) --CO--heteroaryl,n) --CO.sub.2 R.sup.4, oro) protected aldehyde;heteroaryl is defined as a 5- or 6-membered aromatic ring containing 1, 2 or 3 heteroatoms selected from O, N and S, which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3 ;n is: 0 to 5;t is: 0, 1 or 2;R.sup.4 is: H, or C.sub.1 -C.sub.8 alkyl;R.sup.5 is: H, C.sub.1 -C.sub.8 alkyl, or aryl;R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently: H, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkylthio, aryl, each of which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3 ;comprising the following steps:1) adding to a compound of Formula II in a solvent, ##STR37## a solution of phosphate buffer to maintain a pH of about 4.0 to about 8.0;2) maintaining the phosphate-buffered biphasic mixture of the compound of Formula II at about 0.degree. C. to about 50.degree. C.;3) adding sodium chlorite and a catalytic amount of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy, free radical) to the mixture; and4) charging the mixture with a catalytic amount of sodium hypochlorite to oxidize to the compound of Formula I.