Patent ID: 6127573
Filing Date: 2000-10-03
Classification: C07C,C07D

Abstract:
A process for preparing a compound of Formula I:R.sup.1 --CO.sub.2 Hwherein:R.sup.1 is:a) H,b) C.sub.1 -C.sub.8 alkyl,c) C.sub.2 -C.sub.8 alkynyl,d) C.sub.3 -C.sub.7 cycloalkyl,e) aryl,f) heteroaryl, org) heterocyclyl;C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkynyl, or 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.3 -C.sub.8 cycloalkyl, aryl, heteroaryl, heterocyclyl, 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, or 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 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, and CO(CH.sub.2).sub.n CH.sub.3 ;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, CO(CH.sub.2).sub.n CH.sub.3, and additionally the 5- or 6-membered aromatic ring can be benzofused and unsubstituted or substituted with one, two or three substituents as described above;heterocyclyl is defined as a 5- or 6-membered, non-aromatic ring containing 1, 2 or 3 heteroatoms selected from O, N and S, which may contain one or two double bonds and 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, and additionally the 5- or 6-membered ring can be benzofused and unsubstituted or substituted with one, two or three substituents as described above;n is: 0 to 5;t is: 0, 1 or 2;R.sup.4 is: H, or C.sub.1 -C.sub.8 alkyl; orcomprising the following steps:1) adding to a compound of Formula II in a solvent,R.sup.1 --CH.sub.2 OHIIsolution 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 a catalytic amount of TEMPO to the mixture; and4) charging the TEMPO/phosphate-buffered biphasic mixture with a solution of sodium chlorite and a catalytic amount of sodium hypochlorite to oxidize to the compound of Formula I.