Process for preparing AZT

US5466787A · kind A · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Bang-Chi Chen · Cranbury, US
• Sandra L. Quinlan · Manlius, US

Key dates

• Filing date: Nov 15, 1993
• Grant date: Nov 14, 1995
• Expiry date: Nov 15, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for preparing AZT and comprising the steps of: PA1 a) reacting a 2'-halo-5'-protected pyrimidinyl 2'-deoxyribonucleoside having a 3'-sulfonyl group with tributyl tin hydride and catalytic amount of azobisisobutyronitrile in an ether, ester, or ketone solvent to yield a dehalogenated pyrimidinyl 2'-deoxyribonucleoside; followed by PA1 b) reacting said dehalogentated pyrimidinyl 2'-deoxynucleoside formed in step (a) with a base, a lithium salt, and an azide salt to yield a 5'-protected pyrimidinyl 3'-dideoxy-3'-azido-ribonucleoside; and PA1 c) deprotecting the nucleoside derivative of step (b) to yield 3'-dideoxy-3'-azidothymidine.