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Folate analogues: 27. syntheses of 14 carbon‐labeled 10‐deazaaminopterin and 10‐ethyl‐10‐deazaaminopterin
Author(s) -
Nair M. M.,
Nanavati Nitin T.
Publication year - 1987
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.2580240803
Subject(s) - chemistry , moiety , hydrolysis , yield (engineering) , glutamic acid , ethyl ester , amino acid , alkaline hydrolysis , glutamate receptor , acid hydrolysis , organic chemistry , stereochemistry , medicinal chemistry , biochemistry , materials science , receptor , metallurgy
10‐Deazaaminopterin (1) and 10‐Ethyl‐10‐deazaaminopterin ( 2 ) labeled uniformly with 14 C at the glutamate moiety were prepared by the following procedure. Uniformly labeled L‐glutamic acid was converted to its dimethyl ester ( 3 ). 4‐Amino‐4‐deoxy‐10‐deazapteroic acid ( 4 ) and 4‐amino‐4‐deoxy‐10‐ethyl‐10‐deazapteroic acid ( 5 ) were converted to their respective mixed anhydrides 6 and 7 with isobutylchloroformate. Reaction of 6 and 7 with labeled dimethyl‐L‐glutamate gave dimethyl‐10‐deazaaminopterin ( 8 ) and dimethyl 10‐ethyl‐10‐deazaaminopterin ( 9 ) respectively, which on mild alkaline hydrolysis gave the target compounds 1 and 2 in 22 ‐25% yield, based on the amount of radiolabeled glutamic acid used.