First practical resolution of a 3-(4-methoxyphenyl)glycidic acid ester by preferential crystallization and synthesis of diltiazem
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Add time:08/03/2019 Source:sciencedirect.com
Among the various esters of 3-(4-methoxyphenyl)glycidic acid, 4-chloro-3-methylphenyl ester (±)-3 was found to exist as a conglomerate, and could be alternately resolved into (+)- and (−)-3 of >98% ee by a preferential crystallization procedure. Furthermore, a 1,5-benzothiazepine derivative, (+)-6, a significant intermediate of diltiazem, was prepared in one pot in 76% overall yield through the treatment of enantiomerically pure (−)-3 with 2-aminothiophenol followed by a ring closing reaction.
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