Benzoyl chloride → 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

HRID 1089416

Reaction equation

HRID 1089416 reaction equation
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:18]([O:9][C@@H:8]1[C@H:10]([O:11][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:12]([CH3:13])[O:14][C@H:7]1[N:6]1[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]1=[O:16])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18343Doxifluridine

Product 1

HCID 121353572',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5'-deoxy-5-fluorouridine (24.6 g) in dry pyridine (150 ml) was added dropwise 24.5 ml of benzoyl chloride over 10 minutes at 0° C. and the mixture was stirred for 5 hours at room temperature. After removal of pyridine under reduced pressure the residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate - n-hexane to give 38.9 g of 2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine, MS 455 (MH+).

Workup

  1. customAfter removal of pyridine under reduced pressure the residue
  2. customwas partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate - n-hexane

Sources & evidence

ORD record
ord-dbb8ebe7c93d44c590af8e150c619808
Source dataset
uspto-grants-1990_10
Patent number
US04966891

Linked notes

Loading…