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

HRID 1154528Notes

Reaction equation

HRID 1154528 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCOCC1>[C:31]([N:18]1[C:19](=[O:20])[C:21]([F:23])=[CH:22][N:15]([C@@H:7]2[O:8][C@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]2)[C:16]1=[O:17])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 127901643',5'-Di-O-acetyl-2'-deoxy-5-fluorouridine

Product 1

HCID 228287873-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridineYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine and 0.76 ml of triethylamine were dissolved in 10 ml of dry dioxane, and the resulting solution was cooled with ice. To the solution was added 0.65 g of benzoyl chloride, and the resulting mixture was allowed to stand at room temperature for 60 minutes and then at 45° C. for 30 minutes. The crystals formed were filtered off, and the filtrate was concentrated under reduced pressure. The oily residue was purified by column chromatography on silica gel [column, diameter 3.5 cm; length, 21 cm; solvent, chloroform-methanol (99/1)]. The purified oily substance was dissolved in 10 ml of dimethylsulfoxide and added dropwise to 300 ml of water with vigorous agitation to be deposited as a solid. This solid was collected by filtration, washed sufficiently with water and dried at room temperature under reduced pressure. There was obtained 1.04 g (yield: 79.1%) of 3-benzoyl-2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine as powder. The structure was supported by the absorption spectra and elemental analysis.

Workup

  1. temperaturethe resulting solution was cooled with ice
  2. waitat 45° C. for 30 minutes
  3. customThe crystals formed
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe oily residue was purified by column chromatography on silica gel [column, diameter 3.5 cm; length, 21 cm; solvent, chloroform-methanol (99/1)]
  7. dissolutionThe purified oily substance was dissolved in 10 ml of dimethylsulfoxide
  8. additionadded dropwise to 300 ml of water with vigorous agitation
  9. filtrationThis solid was collected by filtration
  10. washwashed sufficiently with water
  11. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-31fd37db3601472792277c32ece20f0f
Source dataset
uspto-grants-1984_12
Patent number
US04490366

Reaction notes

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