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

HRID 1419486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419486
[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].F[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC.[N-:41]=[N+:42]=[N-:43].[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:41]=[N+:42]=[N-:43])[N:17]=[CH:16]2)[C@H:6]1[F:29])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 15736157methyl 2-deoxy-2-fluoro-beta-D-ribofuranosideHCID 538717291-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazole

Produkt 1

HCID 542783091-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino) imidazoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound (38) (60 mg) obtained in item (5) above was dissolved in N,N-dimethylformamide (1.2 ml), to which sodium azide (27 mg) was added and the mixture so obtained was stirred at room temperature for 2 hours. The resulting reaction solution was concentrated and the residue as formed was extracted with chloroform. The solution in chloroform thus formed was washed with water, dried over anhydrous sodium sulfate and then concentrated to afford the titled compound (39) (56 mg) as a syrup. Yield: 92%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-012005f12e424b6e964c1cd53254ad3f
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05886167

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