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

HRID 1419487Notes

Reaction equation

HRID 1419487 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 542783091-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino) imidazole

Product 1

HCID 544024694-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound (39) (50 mg) obtained in item (6) above was dissolved in methanol (2 ml), to which was then added a 0.2M sodium methylate solution (0.2 ml) in methanol. The mixture obtained was allowed to undergo the reaction at room temperature for 20 minutes. The resulting reaction solution was neutralized with addition of ion-exchange resin, Amberlite CG-120 (H+ form) (100-200 mesh) and filtered, and the filtrate was concentrated. The solid residue obtained was washed with diethylether to give the titled compound (40) (31 mg) as an insoluble solid. Yield: 77%.

Workup

  1. customThe mixture obtained
  2. customthe reaction at room temperature for 20 minutes
  3. customThe resulting reaction solution
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe solid residue obtained
  7. washwas washed with diethylether

Sources & evidence

ORD record
ord-1007395822e147008e9c30a74abacbfd
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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