Journal of Organic Chemistry p. 7469 - 7472 (2007)
Update date:2022-09-26
Topics: Chiral Derivative Methyl Amino acid Valine Concise synthesis
Kuethe, Jeffrey T.
Gauthier Jr., Donald R.
Beutner, Gregory L.
Yasuda, Nobuyoshi
(Chemical Equation Presented) A practical and efficient protocol for the three-step synthesis of (S)-N-emoxycarbonyl-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.
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(2007)
