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Synthesis of 3H-etomidate ano resolution into its enantiomers

✍ Scribed by J. J. P. Heykants; A. G. Knaeps; M. A. C. Janssen

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
227 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Etomidate, (R)‐(+)‐ethyl 1‐(1‐phenylethyl)‐1H‐inidazole‐5‐carboxylate, is a short‐acting hypnotic. Tritium was introduced in the ortho‐position of the phenyl‐group by catalytic dehalogenation of the 2‐chloro‐analogue. The homologous tritiated methyester, (+)‐methyl 1‐(1‐phenylethyl)‐1H‐imidazole‐5‐carboxylate, was hydrolyzed to the corresponding carboxylic acid. The resolution into both enantiomers was carried out by successive salt formation with (R)‐(+)‐ and (S)‐(‐)‐α‐methylbenzenemethanamine. After isolation of the diastereoisomeric salts, both enantiomers were obtained by esterification of the salts in ethanol, saturated with HCl‐gas.

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