Synthesis of 2-Benzamido-2-mercaptopropanoic acid from 4-Methyl-2-phenyl-2-oxazolin-5-one

Abstract

The structures of the dimers of N-substituted pyruvamides are confirmed to be the pyrrolidinones (6). 4-Chloro-4-methyl-2-phenyl-2-oxazolin-5-one reacts with a-toluenethiol to give a thiol ester which can be converted into 2-benzamido-2-benzyl-thiopropanoic acid. Reaction of the chlorooxazolinone with thioacetic acid gives 4-acetylthio-4-methyl-2-phenyl-2-oxazolin-one which is converted into 2-benzamido-2-mercaptopropanoic acid. The mercapto acid is oxidized by iron(111) chloride-ether to a mixture of disulphides.