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

C. E. Cook, C. Ray Tallent, Noel Ballentine, George F. Taylor, John A. Kepler

Research output: Contribution to journalArticle

7 Citations (Scopus)

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‐3‐3H)butyl]‐2H‐l‐ benzopyran‐2‐one (R‐ and S‐warfarin‐3′‐3H) of specific activity 31.2 and 24.9 Ci/mmole, respectively. The compounds have been used to develop a stereoselective radioimmunoassay for warfarin enantiomers.

Original languageEnglish (US)
Pages (from-to)623-631
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume16
Issue number4
DOIs
StatePublished - Jan 1 1979

Fingerprint

Enantiomers
Tritium
Warfarin
Liquid Chromatography
Radioimmunoassay
Gases
Liquid chromatography

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

Cook, C. E. ; Tallent, C. Ray ; Ballentine, Noel ; Taylor, George F. ; Kepler, John A. / Synthesis of high specific activity R‐and S‐ warfarin‐3H. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1979 ; Vol. 16, No. 4. pp. 623-631.
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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‐3‐3H)butyl]‐2H‐l‐ benzopyran‐2‐one (R‐ and S‐warfarin‐3′‐3H) 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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Synthesis of high specific activity R‐and S‐ warfarin‐3H. / Cook, C. E.; Tallent, C. Ray; Ballentine, Noel; Taylor, George F.; Kepler, John A.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 16, No. 4, 01.01.1979, p. 623-631.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of high specific activity R‐and S‐ warfarin‐3H

AU - Cook, C. E.

AU - Tallent, C. Ray

AU - Ballentine, Noel

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AU - Kepler, John A.

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AB - 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‐3‐3H)butyl]‐2H‐l‐ benzopyran‐2‐one (R‐ and S‐warfarin‐3′‐3H) 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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