Acetic Anhydride → 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine

HRID 466090Notes

Reaction equation

HRID 466090 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH2:8]([O:15][C@@H:16]1[C@@H](CO)[O:19][C@@H:18]([N:23]2[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[CH2:8]([O:15][C@@H:16]1[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:19][C@@H:18]([N:23]2[CH:30]=[C:29]([F:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

Product 1

HCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridineYield 81.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.33 ml quantity of acetic anhydride was added to a solution of 3.95 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 30 ml of pyridine, and the mixture was left to stand at 40° C overnight. The solvent was distilled off and the residue was dissolved in 30 ml of ethyl acetate. The solution was washed twice with 15 ml of water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was placed on a silica gel column and eluted with chloroform, giving 3.62 g of the title compound in a yield of 81.5%.

Workup

  1. waitthe mixture was left
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  4. washThe solution was washed twice with 15 ml of water
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-ae968815880647bea357d818309643a7
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

Loading…