Benzoyl chloride → 3'-O-benzoyl-5'-deoxy-5-fluorocytidine

HRID 1089419Notes

Reaction equation

[F:1][C:2]1[C:3]([NH2:17])=[N: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:11][C@@H:10]1[C@@H:12]([CH3:13])[O:14][C@@H:7]([N:6]2[CH:15]=[C:2]([F:1])[C:3]([NH2:17])=[N:4][C:5]2=[O:16])[C@@H:8]1[OH:9])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5'-Deoxy-5-fluorocytidine (245 mg) was dissolved in dry pyridine (5 ml). To the solution was added benzoyl chloride (130 μl) with stirring at 0° C. The reaction mixture was stirred for 1 hour at 0° C. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (dichloromethane - methanol) followed by recrystallization from ethyl acetate to give colorless crystals of 3'-O-benzoyl-5'-deoxy-5-fluorocytidine (51 mg). mp 127°~129° C.; MS 350 (MH+).

Workup

stirringThe reaction mixture was stirred for 1 hour at 0° C
customAfter removal of the solvent under reduced pressure
customthe residue was purified by silica gel column chromatography (dichloromethane - methanol)
customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record: ord-21db75f41ff04485a52c86992fd4b3d6
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04966891

Reaction notes

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