Ethanol → 5'-O-Acetyl-2',3'-dideoxy-3'-fluorouridine

HRID 466736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466736
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[F:8][C@@H:9]1[C@@H](CO)[O:12][C@@H:11]([N:16]2[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1.C(O)C>N1C=CC=CC=1>[C:5]([O:4][CH2:1][C@H:2]1[O:12][C@@H:11]([N:16]2[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10][C@@H:9]1[F:8])(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 1624502',3'-Dideoxy-3'-fluorouridine

Produkt 1

HCID 131215805'-O-Acetyl-2',3'-dideoxy-3'-fluorouridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Acetic anhydride (1.2 ml, 13 mmol) was added to a solution of 2',3'-dideoxy-3'-fluorouridine (1 g, 4.34 mmol) in dry pyridine (10 ml) and the mixture was stirred at room temperature for 24 hours. Ethanol (2 ml) was added and the mixture was evaporated to dryness. Residual pyridine was removed by coevaporation with portions of ethanol and the final residue purified by silica gel column chromatography eluting with 5% MeOH/CH2Cl2 to give the title compound which was isolated following trituration with ether.

Aufarbeitung

  1. customthe mixture was evaporated to dryness
  2. customResidual pyridine was removed by coevaporation with portions of ethanol
  3. customthe final residue purified by silica gel column chromatography
  4. washeluting with 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4e3af2f14c7b4ada8a2d95fee6fde7aa
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157114

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