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Synthesis of high specific activity R-and S- warfarin-3H

✍ Scribed by C. E. Cook; C. Ray Tallent; Noel H. Ballentine; George F. Taylor; John A. Kepler

Publisher
John Wiley and Sons
Year
1979
Tongue
French
Weight
358 KB
Volume
16
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

4‐Hydroxy‐3‐[3‐oxo‐1‐(3‐bromophenyl)butyl]‐2H‐1‐benzopyran‐2‐one (3′ ‐bromowarfarin) was synthesized and resolved into its enantiomers by formation of the d‐10‐camphorsulfonate diastereoisomers, which were separated by liquid chromatography and hydrolyzed. The pure enantiomers were reduced with tritium gas to yield R‐ and S‐4‐hydroxy‐3‐[3‐oxo‐1‐(phenyl‐3‐^3^H)butyl]‐2H‐l‐ benzopyran‐2‐one (R‐ and S‐warfarin‐3′‐^3^H) of specific activity 31.2 and 24.9 Ci/mmole, respectively. The compounds have been used to develop a stereoselective radioimmunoassay for warfarin enantiomers.

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