Conditions:-

i. N-(2-chloro-1,1,2-trifluoroethyl)diethyl amine, Dimethyl formamide, 70 °C, 30 min, ii. Sodium azide, dimethyl formamide, water, reflux, 5 h

Drug Synthe




General Category

Zidovudine

CAS No:- [30516-87-1]

IUPAC Name:- 3¢-Azido-3¢-deoxythymidine

M. P.:- 121-22 °C

MW: 267.24

Drug information:- Zidovudine is an anti-microbial drug further classified as anti-viral agent. It is used either signally or in combination with other drugs for the treatment of human immunodeficiency virus (HIV) and even AIDS. The drug inhibits the formation of DNA in new cells thereby inhibiting raplication of the virus

Schematic Representation for Synthesis of Zidovudine

Preparation of Zidovudine is described in US Patent 4,724,232. Accordingly, 1-[(2R,4R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione 1 was treated with N-(2-chloro-1,1,2-trifluoroethyl)diethyl amine using dimethyl formamide as solvent at elevated temperatures to give intermediate compound 2. Heating 2 with sodium azide using dimethyl formamide and water as solvent mixture at reflux temperature affords 1-[(2R,4R)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione also called Zidovudine 3.