Issue 3, 1996

An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

Abstract

The treatment of the N-benzyloxycarbonyl α-methyl esters of L-glutamine or L-asparagine with tert-butyl nitrite in refluxing acetonitrile results in selective hydrolysis of the amide group, giving optically pure Z-Glu-OMe (74%) or Z-Asp-OMe (88%); these are versatile chiral building blocks, and an efficient synthesis of cis-5-hydroxy-L-pipecolic acid from Z-Glu-OMe is described.

Article information

Article type
Paper

Chem. Commun., 1996, 349-350

An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid

D. R. Adams, P. D. Bailey, I. D. Collier, J. D. Heffernan and S. Stokes, Chem. Commun., 1996, 349 DOI: 10.1039/CC9960000349

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements