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Note | Regular issue | Vol 55, No. 5, 2001, pp.961-966
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9175
Mechanistic Studies on Racemization of Chiral 2-Arylthiazolidinons

Tatsuya Kato* and Tomokazu Ozaki

*Fiji Gotemba Research Laboratories, Chugai Pharmaceutical Company, Ltd., 135, 1-Chome Komakado, Gotemba City, shizuoka 412-8513, Japan

Abstract

Mechanistic studies on racemization of chiral 3-[(2S)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propanoic acid is described. This racemization is triggered by deprotonation of phenolic hydroxyl group. We propose that the racemization proceeds via a novel mechanism involving ring opening-closure equilibrium of the thiazolidinone ring.