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Synthesis of edatrexate (2‐ 13 C‐glutamate)
Author(s) -
DeGraw Joseph I.,
Colwell William T.,
Jue Thomas
Publication year - 1997
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/(sici)1099-1344(199702)39:2<99::aid-jlcr949>3.0.co;2-#
Subject(s) - chemistry , saponification , yield (engineering) , reagent , column chromatography , nuclear magnetic resonance spectroscopy , chemical synthesis , glutamate receptor , carbon 13 nmr , stereochemistry , nuclear chemistry , organic chemistry , in vitro , biochemistry , receptor , materials science , metallurgy
The experimental antitumor drug Edatrexate, labeled with 99% 13 C at the 2‐position of the glutamate acid group was required for 13 C‐magnetic resonance spectroscopy studies in biological media. Coupling of 2,4‐diamino‐4‐deoxy‐10‐ethyl‐10‐deazapteroic acid with diethyl L‐2‐ 13 C‐glutamate as promoted by BOP reagent afforded Edatrexate (2‐ 13 C‐glu) diethyl ester in 60% yield following purification by column chromatography. Saponification by aqueous NaOH in 2‐methoxyethanol gave the target molecule in 44% yield or 26% overall. © 1997 John Wiley & Sons, Ltd.