Lithium azide → Zidovudine

HRID 2108150Notes

Reaction equation

HRID 2108150 reaction equation
[CH3:1][C:2]1[C:15](=[O:16])[N:14]=[C:13]2[N:4]([C@@H:5]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:7]([O:12]2)[CH2:6]3)[CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Li+]>CN(C)C(=O)C>[N:17]([C@@H:7]1[C@@H:8]([CH2:10][OH:11])[O:9][C@@H:5]([N:4]2[CH:3]=[C:2]([CH3:1])[C:15](=[O:16])[NH:14][C:13]2=[O:12])[CH2:6]1)=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 69157522,3'-Anhydrothymidine

Product 1

HCID 35370ZidovudineYield 80%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

2,3'-Anhydrothymidine (0.673 g, 3.0 mmol), lithium azide (0.4 g, 9.0 mmol) and N,N-dimethylacetamide (7.5 ml) were heated together with stirring at 130° C. for 16 hr. The products were then worked-up and chromatographed on silica gel to give 3'-azido-3'-deoxythymidine (0.64 g, 80%). identical to authentic material.

Workup

  1. customworked-up and chromatographed on silica gel

Sources & evidence

ORD record
ord-81abb7472e6043c8870c9f2dfc844e51
Source dataset
uspto-grants-1990_06
Patent number
US04937329

Reaction notes

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