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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2007-09, Vol.72 (19), p.7469-7472
Hauptverfasser: Kuethe, Jeffrey T, Gauthier, Donald R, Beutner, Gregory L, Yasuda, Nobuyoshi
Format: Artikel
Sprache:eng
Schlagworte:
Valine - analogs & derivatives
Valine - chemical synthesis
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Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7012862