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Asymmetric synthesis of ( R )‐(+)‐[[(2‐bromoethyl)amino]methyl]‐2‐nitro‐1H‐imidazole‐[1‐ 14 C]‐ethanol monohydrobromide
Author(s) -
Ekhato I. Victor
Publication year - 1998
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(199806)41:6<523::aid-jlcr105>3.0.co;2-i
Subject(s) - chemistry , barium carbonate , nitro , yield (engineering) , imidazole , enantioselective synthesis , ethanol , carbonate , nitro compound , stereochemistry , medicinal chemistry , organic chemistry , catalysis , raw material , alkyl , materials science , metallurgy
The enantioselective synthesis of ( R )‐(+)‐2‐( tert ‐butyldiphenylsiloxylmethyl)[ 14 C]oxirane from 14 C‐labeled barium carbonate was accomplished. This labeled oxirane facilitated an asymmetric synthesis ( R )‐(+)‐[[‐bromoethyl)amino]methyl]‐2‐nitro‐1H‐imidazole‐[1‐ 14 C]‐ethanol monohydrobromide (CI‐1010), a potent hypoxic cell selective radiosensizing anti‐cancer agent. From labeled barium carbonate the labeled oxirane was prepared in 26.2% yield, and this gave the target labeled CI‐1010 in 17% yield. © 1998 John Wiley & Sons, Ltd.