A Concise Synthesis of (S)-N-Ethoxycarbonyl-α-methylvaline
- 22 August 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (19) , 7469-7472
- https://doi.org/10.1021/jo7012862
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.Keywords
This publication has 18 references indexed in Scilit:
- Role of Secondary Structure in the Asymmetric Acylation Reaction Catalyzed by Peptides Based on Chiral Cα-Tetrasubstituted α-Amino AcidsThe Journal of Organic Chemistry, 2004
- Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximesChiral oxime ethers in asymmetric synthesis. Part 6.1Organic & Biomolecular Chemistry, 2003
- L‐Phenylalanine Cyclohexylamide: A simple and convenient auxiliary for the synthesis of optically pure α,α‐disubstituted (R)‐ and (S)‐amino acidsHelvetica Chimica Acta, 1995
- A New General Approach to Enantiomerically Pure Cyclic and Open‐Chain (R)‐ and (S)‐α,α‐Disubstituted α‐Amino AcidsHelvetica Chimica Acta, 1992
- Synthesis of optically pure .alpha.-alkylated .alpha.-amino acids and a single-step method for enantiomeric excess determinationThe Journal of Organic Chemistry, 1988
- Synthese von 4,4‐disubstituierten 1,3‐Thiazol‐5(4H)‐thionenHelvetica Chimica Acta, 1986
- α‐Alkylation of Amino Acids without Racemization. Preparation of Either (S)‐ or (R)‐α‐Methyldopa from (S)‐AlanineHelvetica Chimica Acta, 1985
- Carbonyl oxide chemistry. The NIH shiftJournal of the American Chemical Society, 1984
- .alpha.-Methyl amino acids. Resolution and amino protectionThe Journal of Organic Chemistry, 1975
- Synthesis of L-.alpha.-methyldopa from asymmetric intermediatesThe Journal of Organic Chemistry, 1968