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Synthesis of tritium‐labelled metabolites of ibuprofen
Author(s) -
Shyadehi Akbar Z.,
Harding John J.
Publication year - 1999
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(199903)42:3<207::aid-jlcr210>3.0.co;2-5
Subject(s) - chemistry , tritium , decarboxylation , moiety , malonic acid , carbon 14 , metabolite , tritium illumination , hydrogen , catalysis , carbon fibers , medicinal chemistry , organic chemistry , physics , materials science , quantum mechanics , composite number , nuclear physics , composite material , biochemistry
The two major metabolites of ibuprofen, 2‐[4‐(2‐carboxypropyl)phenyl]propionic acid and 2‐[4‐(2‐methyl‐2‐hydroxypropyl)phenyl]propionic acid, were labelled with tritium. The hydroxy‐metabolite containing tritium at α‐ and β‐carbons of the propionic acid moiety was prepared by catalytic reduction of the olefinic double bond in 2‐[4‐(2‐methyl‐2‐hydroxypropyl)phenyl]propionic acid with tritium‐enriched hydrogen. Tritium‐labelling at the two carbon atoms α to the two carboxyl groups of the carboxy‐metabolite was achieved by initially exchanging the carboxyl hydrogens of the corresponding dimalonic acid derivative synthesised in this work, followed by its decarboxylation. In this process one of the carboxyl groups of each of the malonic acid components is lost as carbon dioxide, transferring its tritium/hydrogen atom to the α‐carbon. Copyright © 1999 John Wiley & Sons, Ltd.