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

HRID 965389

Reaktionsgleichung

Reaktionsgleichung von HRID 965389
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]

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c5894fee5415438d9993ce76ab956ba8
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773607

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