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Synthesis of carbon‐14 labelled xenalipin ‐ a potential hypolipidemic agent
Author(s) -
Hill John A.,
Eaddy John F.
Publication year - 1992
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.2580311208
Subject(s) - chemistry , oxazoline , benzoic acid , carbon 14 , hydrolysis , derivative (finance) , trifluoromethyl , specific activity , chemical synthesis , metabolism , palladium , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , biochemistry , enzyme , in vitro , physics , alkyl , quantum mechanics , financial economics , economics
Xenalipin 1 (4′‐trifluoromethyl‐2‐biphenylcarboxylic acid) was synthesized in the [ 14 C]‐labelled form with specific activity 21.0 mCi/mmol suitable for metabolism and distribution studies in animals. The synthetic sequence involved conversion of [ 14 C]‐ benzoic acid to the 4,4‐dimethyl‐2‐oxazoline derivative, formation of an organozinc compound, palladium‐catalyzed coupling of the arylzinc‐oxazoline with 4‐trifluoromethyliodobenzene, and acid hydrolysis. The radiochemical purity was 99.4%.