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Synthesis of [1′,3′,4′‐ 3 H 3 ]4‐(5′,6′,7′,8′‐tetrahydro‐5′,5′,8′,8′‐tetramethyl‐2′‐anthracenyl)benzoic acid for binding studies of retinoic acid receptors
Author(s) -
Dawson Marcia I.,
Hobbs Peter D.,
Rhee Sung W.,
Morimoto Hiromi,
Williams Philip G.
Publication year - 1993
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.2580330710
Subject(s) - chemistry , benzoic acid , tritium , halogenation , hydrolysis , medicinal chemistry , nuclear magnetic resonance spectroscopy , ring (chemistry) , palladium , nuclear chemistry , radiochemistry , stereochemistry , organic chemistry , catalysis , physics , nuclear physics
[1′,3′,4′‐ 3 H 3 ]4‐(5′,6′,7′,8′‐Tetrahydro‐5′,5′,8′,8′‐tetramethyl‐2′‐anthracenyl)benzoic acid (specific activity 64 Ci/mmole) was synthesized by bromination of ethyl 4‐(5′,6′,7′,8′‐tetrahydro‐5′,5′,8′,8′‐tetramethyl‐2′‐antracenyl)benzoate, followed by reductive debromination by tritium gas in the presence of 10% palladium on carbon and hydrolysis. 1 H and 3 H NMR spectroscopy was used to establish tritium at 1′,3′,4′‐tetrahydroanthracenyl ring positions.