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
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Sprache:eng
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Valine - analogs & derivatives
Valine - chemical synthesis
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container_end_page 7472
container_issue 19
container_start_page 7469
container_title Journal of organic chemistry
container_volume 72
creator Kuethe, Jeffrey T
Gauthier, Donald R
Beutner, Gregory L
Yasuda, Nobuyoshi
description 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.
doi_str_mv 10.1021/jo7012862
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subjects Valine - analogs & derivatives
Valine - chemical synthesis
title A Concise Synthesis of (S)-N-Ethoxycarbonyl-α-methylvaline
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