Preparation of optically active 2-thiazolidinecarboxylic acid by asymmetric transformation

Article abstract of DOI:10.1248/cpb.47.1180

Cysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R,3R)- or (2S,3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2- thiazolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC. The (-)- and (+)- 2-THC obtained were determined to be enantiopure forms by comparing their powder X-ray diffraction patterns with that of (RS)-2-THC. The absolute configurations of (-)- and (+)-2-THC were estimated based on molar rotations of (2R,4R)- and (2S,4R)-2,4- thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and (-)- and (+)-2-THC. ()-2THC was determined to have the (R)-configuration, and (+)- 2-THC to have the (S)-configuration.

Full text of DOI:10.1248/cpb.47.1180

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