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Synthesis of 3 H and 14 C labeled (S)‐3‐(5‐chloro‐2‐methoxyphenyl)‐1,3‐dihydro‐3‐fluoro‐6‐(trifluoromethyl)‐2H‐indol‐2‐one, maxipost™. An agent for post‐stroke neuroprotection
Author(s) -
Dischino Douglas D.,
Gribkoff Valentin K.,
Hewawasam Piyasena,
Luke George M.,
Rinehart J. Kent,
Spears Tony L.,
Starrett John E.
Publication year - 2003
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.652
Subject(s) - chemistry , trifluoromethyl , yield (engineering) , enantiomer , high performance liquid chromatography , chemical synthesis , carbon 14 , specific activity , carboxylate , medicinal chemistry , stereochemistry , organic chemistry , in vitro , biochemistry , alkyl , materials science , metallurgy , enzyme , physics , quantum mechanics
The syntheses of tritium labeled ( S )‐3‐(5‐chloro‐2‐[OC 3 H 3 ]methoxyphenyl‐1,3‐dihydro‐3‐fluoro‐6‐(trifluoromethyl)‐1H‐indol‐2‐one, and carbon‐14 ( S )‐3‐(5‐chloro‐2‐methoxyphenyl)‐1,3‐dihydro‐3‐fluoro‐6‐(trifluoromethyl)‐2H‐[2,3‐ 14 C 2 ] indol‐2‐one are reported. The 3 H‐labeled compound was prepared in a two‐step synthesis from C 3 H 3 I. The final product was purified via chiral HPLC to yield the desired enantiomer in a 4% radiochemical yield and a specific activity of 60 Ci/mmol. The 14 C‐labeled compound was prepared in a four‐step synthesis from diethyl [carboxylate‐ 14 C 1 , 2 ] oxalate. The final product was purified via chiral HPLC to yield the desired enantiomer in a 20% radiochemical yield and a specific activity of 28.4 μCi/mg. Copyright © 2002 John Wiley & Sons, Ltd.