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Synthesis of tritium‐labeled DL‐γ‐carboxyglutamic acid and its cyclic form 5‐oxo‐2,4‐pyrrolidine dicarboxylic acid
Author(s) -
Ishikawa Yoshinori,
Wuthier Roy E.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210604
Subject(s) - chemistry , pyrrolidine , cyclohexylamine , hydrolysis , dicarboxylic acid , tritium , salt (chemistry) , alkaline hydrolysis , organic chemistry , nuclear chemistry , physics , nuclear physics
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 γ‐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 γ‐carboxyglutamic acid (4.9 Ci/mmol) and its cyclic form (6.1 ci/mmol).