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

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

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被引用次数: 12

摘要

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.