A Concise Synthesis of (S)-N-Ethoxycarbonyl-α-methylvaline

…, DR Gauthier, GL Beutner, N Yasuda

Index: Kuethe, Jeffrey T.; Gauthier Jr., Donald R.; Beutner, Gregory L.; Yasuda, Nobuyoshi Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7469 - 7472

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Citation Number: 21

Abstract

A practical and efficient protocol for the three-step synthesis of (S)-N-ethoxycarbonyl-α- methylvaline 3 is described which utilizes readily available commercial starting materials. The key transformations involve resolution-crystallization of tartrate salt 6 followed by a one- pot procedure for the preparation of 3 which is isolated as the dicyclohexylamine salt in 45% overall yield and in 91-95% ee.