Sodium Azide → 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino)imidazole

HRID 1419480Notes

Reaction equation

HRID 1419480 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[C:18]([C:25](=[O:28])[CH2:26]Cl)[N:17]=[CH:16]2)[C@@H:6]1[F:29])(=[O:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[C:18]([C:25](=[O:28])[CH2:26][N:30]=[N+:31]=[N-:32])[N:17]=[CH:16]2)[C@@H:6]1[F:29])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 538717281-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazole

Product 1

HCID 542783081-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino)imidazoleYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (21) (177 mg) obtained in item (10) above was dissolved in N,N-dimethylformamide (3.5 ml), to which sodium azide (80 mg) was added, and the resulting mixture was stirred at room temperature for 2 hours. The reaction solution as formed was concentrated and the residue thus obtained was extracted with chloroform. The solution in chloroform was washed with water, dried over anhydrous sodium sulfate and concentrated to yield the titled compound (22) (153 mg) as a syrup. Yield: 85%.

Workup

  1. additionwas added
  2. customThe reaction solution as formed
  3. concentrationwas concentrated
  4. customthe residue thus obtained
  5. extractionwas extracted with chloroform
  6. washThe solution in chloroform was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8d5adf5cc38c41e69fa9d768c17ae6b0
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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