Synthesis and characterization of N-bromoacetyl-3,3'5-triiodo-L-thyronine using high speed countercurrent chromatography

US5169984A · kind A · utility

Assignee

• The United States of America, as represented by the Department of Health and Human Services · US

Inventors

• Hans J. Cahnmann · Bethesda, US
• Yoichiro Ito · Bethesda, US

Key dates

• Filing date: Sep 10, 1990
• Grant date: Dec 8, 1992
• Expiry date: Sep 10, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C231/24
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A method for synthesizing N-bromoacetyl-3,3',5-triiodo-L-thyronine which involves subjecting 3,3', 5-triiodo-L-thyronine to a one-step bromacetylation reaction wherein 3,3', 5-triiodo-L-thyronine and bromoacetyl bromide are refluxed together in a solution of ethyl acetate. After formation the N-bromoacetyl-3,3'-triiodo-L-thyronine is purified by fractionation utilizing high speed countercurrent chromatography. Labeled N-bromoacetyl-3,3'-5-triiodo-L-thryonine may be made by a one-step bromacetylation reaction by reducing either [.sup.125 I]T.sub.3 or [.sup.14 C]T.sub.3 with bromoacetyl bromide.