Synthesis of tritium-labeled DL-γ-carboxyglutamic acid and its cyclic form 5-oxo-2,4-pyrrolidine dicarboxylic acid

✍ Scribed by Yoshinori Ishikawa; Roy E. Wuthier

• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: French
• Weight: 407 KB
• Volume: 21
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580210604

✦ Synopsis

By condensing diethyl ethoxymethylenemalonate with diethyl acetamidomalonate, 5-hydroxy-2,4-dicarbethoxypyrrole was prepared. Hydrogenation over Pt-C to 5-oxo-2,4-dicarbethoxypyrrolidine, followed by alkaline hydrolysis gave y-carboxyglutamate. Mild alkaline hydrolysis yielded 5-oxo-2,4-pyrrolidine dicarboxylic acid which was isolated as the cyclohexylamine salt. These procedures were applied to prepare tritium-labeled y-carboxyglutamic acid ( 4 . 9

Ci/mmol) and its cyclic form (6.1 ci/mmol).