Sodium citrate, potassium citrate, citric acid → 4-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazole

HRID 1419481Notes

Reaction equation

HRID 1419481 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11]C(=O)C)[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:30])[CH2:26][N:27]=[N+:28]=[N-:29])[N:17]=[CH:16]2)[C@@H:6]1[F:31])(=O)C.C[O-].[Na+].C(C(O)(C([O-])=O)CC([O-])=O)C([O-])=O.C(C(O)(C([O-])=O)CC([O-])=O)C([O-])=O.O.[Na+].[Na+].[Na+].[K+].[K+].[K+]>CO>[N:27]([CH2:26][C:25]([C:18]1[N:17]=[CH:16][N:15]([C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:5]([OH:4])[C@H:6]2[F:31])[C:19]=1[N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[O:30])=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 171403Sodium citrate, potassium citrate, citric acidHCID 10942334Sodium MethoxideHCID 542783081-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino)imidazole

Product 1

HCID 544024704-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound (22) (130 mg) obtained in item (11) above was dissolved in methanol (6 ml), to which was added a 0.2M sodium methylate solution (0.5 ml) in methanol and the resulting mixture was allowed to stand at room temperature for 30 minutes. The reaction solution as formed was neutralized with addition of ion-exchange resin, Amberlite CG-120 (H+ form) (100-200 mesh), filtered and the filtrate was concentrated to give a solid material which was then washed with diethylether to afford the titled compound (23) (63 mg) as an insoluble substance. Yield: 60%.

Workup

  1. customThe reaction solution as formed
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customto give a solid material which
  5. washwas then washed with diethylether

Sources & evidence

ORD record
ord-e46fbdfc8ba84536a88775171d302229
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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