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Synthesis of flutamide‐d 7 and its main metabolite‐d 6
Author(s) -
Passarella D.,
Martinelli M.,
Passarotti C. M.,
Valenti M.
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<275::aid-jlcr187>3.0.co;2-z
Subject(s) - chemistry , carboxylation , flutamide , metabolite , fluoride , derivative (finance) , medicinal chemistry , nitro , acetyl chloride , chloride , organic chemistry , catalysis , inorganic chemistry , biochemistry , medicine , androgen receptor , alkyl , prostate cancer , cancer , financial economics , economics
With the main objective of examining the pharmacokinetics of flutamide, flutamide‐d 7 and its main metabolite‐d 6 have been prepared. By carboxylation of Grignard‐derivative (IV), deuterocarboxylic acid (V) was prepared from which acyl chloride (VI) was obtained by reaction with (COCl) 2 . Subsequent reaction of (VI) with 4‐nitro‐3‐trifluoromethylaniline afforded (I). Compound (X) was obtained starting from hydroxyacid (IX), through reaction with TMSCl, (COCl) 2 and subsequent condensation with 4‐nitro‐3‐trifluoromethylaniline. Desilylation of (X) by tetrabutylammonium fluoride, gave (II). Copyright © 1999 John Wiley & Sons, Ltd.