Dimethylformamide dimethyl acetal → HCID 22845792, compound

HRID 1885522Notes

Reaction equation

HRID 1885522 reaction equation
[N:1]([C@@:4]1([OH:20])[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].[CH3:21]OC(OC)N(C)C>C(Cl)(Cl)Cl>[CH3:21][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@@:4]([N:1]=[N+:2]=[N-:3])([OH:20])[CH2:5]2)[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 21115113HCID 21115113, compound

Product 1

HCID 22845792HCID 22845792, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3'-Azidothymidine (0.5 g; 1.9 mMol) and N,N-dimethylformamide dimethylacetal (Zemlicksa, Coll. Czech. Chem. Comm. 35, 3572 (1972)) (0.9 mL; 7.5 mMol) were refluxed to 20 mL CHCl3 for 48 hours. The solvent was removed in vacuo and the material placed on a silica column. 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-89035071bde74f848719d6381c1fc876
Source dataset
uspto-grants-1992_09
Patent number
US05145840

Reaction notes

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