Benzoyl chloride → 5'-O-acetyl-3'-O-benzyl-3-benzoyl-2'-deoxy-5-fluorouridine

HRID 466089Notes

Reaction equation

HRID 466089 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>O1CCOCC1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:18]=[C:17]([F:19])[C:15](=[O:16])[N:14]([C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136874845'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine

Product 1

HCID 137150635'-O-acetyl-3'-O-benzyl-3-benzoyl-2'-deoxy-5-fluorouridineYield 78.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.20 g of 5'-O-acetyl-3'-O-benzyl-2'-deoxy-5-fluorouridine in 10 ml of dioxane were added 0.29 g of benzoyl chloride and 0.73 ml of triethylamine, and the mixture was left to stand at 80° C. for 2 hours. The solvent was distilled off and the residue was dissolved in 50 ml of ethyl acetate. The solution was washed with 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 0.2 g of the title compound as an oil in a yield of 78%.

Workup

  1. waitthe mixture was left
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  4. washThe solution was washed with 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-6c3152b55b2a45d389f0975f24c7387d
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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