Zidovudine → HCID 454163, compound

HRID 973790Notes

Reaction equation

HRID 973790 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].[CH3:20]OC(OC)N(C)C>C(Cl)(Cl)Cl>[CH3:20][N:14]1[C:15](=[O:16])[C:17]([CH3:18])=[CH:19][N:11]([C@@H:6]2[O:7][C@H:8]([CH2:9][OH:10])[C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:5]2)[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 35370ZidovudineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 454163HCID 454163, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3'-Azido-3'-deoxythymidine (0.5 g; 1.9 mMol) and N,N-dimethylformamide dimethylacetal (Zemlicka, Coll. Czech. Chem. Comm. 35, 3572 (1972)) (0.9 mL; 7.5 mMol) were refluxed in 20 mL CHCl3 for 48 hours. The solvent was removed in vacuo and the material placed on a silica solumn. Elution with EtOAc/CHCl3 (1:1 v/v) resulted in pure material as a viscous oil: 0.26 g (0.9 mMol, 47%).

Workup

  1. customThe solvent was removed in vacuo
  2. washElution with EtOAc/CHCl3 (1:1 v/v)
  3. customresulted in pure material as a viscous oil

Sources & evidence

ORD record
ord-3a0abe334113499fa03b1dbffe63366d
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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