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Synthesis of carbon‐14 labelled CD 271 (6‐[3‐(1‐adamantyl)‐4‐methoxyphenyl]‐2‐naphthoic acid) a potential new agent for dermatology
Author(s) -
Pilgrim W. R.,
Nedoncelle P.,
Frideling JP.,
Shroot B.
Publication year - 1991
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.2580290715
Subject(s) - chemistry , saponification , catalysis , medicinal chemistry , aryl , ring (chemistry) , benzene , stereochemistry , coupling reaction , chemical synthesis , organic chemistry , alkyl , biochemistry , in vitro
6‐[3‐(1‐Adamantyl)‐4‐methoxyphenyl]‐2‐naphthoic acid ( 1 ), a promising new compound for the treatment of disorders of keratinization, has been synthesized in [ 14 C]‐labelled form from barium [ 14 C]‐carbonate via labelled benzene. Benzene‐[U‐ 14 C] was converted to 4‐bromo‐methoxybenzene‐[phenyl‐U‐ 14 C] in six steps. Introduction of the adamantyl ring was carried out using 1‐acetoxyadamantane under acid catalysis. 2‐(1‐Adamantyl)‐4‐bromo‐methoxybenzene‐[phenyl‐U‐ 14 C] ( 2 ) was converted to a zincate and coupled with methyl 6‐bromo‐2‐naphthoate using a nickel catalyst. The product of the aryl coupling reaction ( 3 ) was then saponified to give 6‐[3‐(1‐adamantyl)‐4‐methoxyphenyl‐[phenyl‐U‐ 14 C]]‐2‐naphthoic acid.