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

HRID 466736Notes

Reaction equation

HRID 466736 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e3af2f14c7b4ada8a2d95fee6fde7aa
Source dataset
uspto-grants-1992_10
Patent number
US05157114

Reaction notes

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