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

HRID 965389Notes

Reaction equation

HRID 965389 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-c5894fee5415438d9993ce76ab956ba8
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

Loading…