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

…, PD Bailey, ID Collier, JD Heffernan, S Stokes

Index: Adams, David R.; Bailey, Patrick D.; Collier, Ian D.; Heffernan, John D.; Stokes, Stephen Chemical Communications, 1996 , # 3 p. 349 - 350

Full Text: HTML

Citation Number: 12

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.

Related Articles:

… kN] ethyl] amino-kN]-4-(carboxy-kO)-1-oxobutyl] amino]-12-hydroxycholan-24-oato (6-)] gadolinate (3-)], a Gd (III) Complex under Development As a Contrast Agent for …

[Anelli, Pier Lucio; Brocchetta, Marino; Lattuada, Luciano; Manfredi, Giuseppe; Morosini, Pierfrancesco; Murru, Marcella; Palano, Daniela; Sipioni, Marco; Visigalli, Massimo Organic Process Research and Development, 2009 , vol. 13, # 4 p. 739 - 746]

Convenient N-Protection of L-Pyroglutamic Acid Esters

[Jain, Rahul Organic Preparations and Procedures International, 2001 , vol. 33, # 4 p. 405 - 409]

Chiral synthesis of trans-1-aminoindolo [2, 3-a] quinolizidine and trans-1-aminobenzo [a] quinolizidine derivatives from L-pyroglutamic acid

[Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon Journal of Organic Chemistry, 1999 , vol. 64, # 26 p. 9727 - 9730]

More Articles...