Method for producing (+) (2S,3S)-3-(2-aminophenylthio)-2-hydroxy

Details Method for producing (+) (2S,3S)-3-(2-aminophenylthio)-2-hydroxy Method for producing (+) (2S,3S)-3-(2-aminophenylthio)-2-hydroxy

1997-03-27

2000-10-10

Kumar, Shailendra

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

562431, C07B 5500, C07C32128

Patent

active

061303526

ABSTRACT:
A process for the preparation of (+) (2S, 3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4'-methoxyphenyl)-propionic acid which comprises treating the (.+-.) compound of (2RS, 3RS) 3-(2-aminophenylthio)-2-hydroxy-3-(4'-methoxyphenyl)-propionic acid (formula (II)) with the (+) compound of the 2-methylbenzylamine (formula (III)) and an alkali in the presence of a polar solvent, the amount of the compound of the formula (III) and the alkali being in half equivalent amount of compound of the formula (II) employed, separating the precipitate (+) amine salt form of (2-aminophenylthio)-2-hydroxy-3-(4'-methoxyphenyl)-propionic acid from the 1(-) salt form remaining in solution, by known methods treating the (+) amine salt from with an organic solvent and then decomposing the (+) amine salt form to produce (+)(2s, 3s)-3-(2-aminophenylthio)-2-hydroxy-3-(4'-methoxyphenyl)-propionic acid.

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E.J.Corey and John Mann, A New Stereocontrolled Synthesis of Prostaglandins via Prostaglandin A.sub.2, Journal of the American Chemical Society, Oct. 3, 1973, pp. 6832-6833.
Merck Research Laboratories, The Merck Index, 1996, p. 1031.

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