Patent ID: 6794516
Filing Date: 2004-09-21
Classification: A61P,C07B,C07C,C07D

Abstract:
A process for forming a substituted aryl oxazoline compound of Formula Ia: whereinR1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkaryl, aralkyl, where the ring portion of said aryl, aralkyl, or alkazyl can be optionally substituted; R3 is alkyl, cycloalkyl, aryl, alkaryl, any of which can be optionally substituted; and R4 is optionally substituted aryl or optionally substituted heteroazyl; said method comprising: (a) asymmetrically dihydroxylating an alkene intermediate of Formula XV: â€ƒto form an optically active diol of Formula XVIa: (b) reacting said optically active diol of Formula XVIa with an orthoester under acid catalysis to give a mixed orthoester, and thereafter reacting the resulting mixed orthoester intermediate with a reagent selected from the group consisting of acyl halides, HCl, HBr, HI, Me3SiCl, Me3Sil, Me3SiBr and halogen-containing Lewis acids to form a haloester derivative of Formula XVIIa: â€ƒwherein X is Cl Br, or I; (c) reacting said haloester derivative with an alkali metal azide to form an azide of Formula XVIIIa: