4-Methylbenzoyl Chloride → 2',3'-Dideoxy-3'-fluoro-5'-O-p-toluoyluridine

HRID 1614684Notes

Reaction equation

[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)=[O:24])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 2',3'-dideoxy-3'-fluorouridine (1 g, 4.34 mmoles) in dry pyridine (25 ml) at 0° C. was slowly added freshly distilled p-toluoyl chloride (0.63 ml, 4.78 mmoles). After the addition was complete, the mixture was stirred at 50° C. for 1.5 hrs., cooled and the solvent removed under reduced pressure. The residue was dissolved in chloroform (35 ml) and the solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml) and dried (sodium sulphate). Evaporation of the solvent and purification of the residue by silica column chromatography eluting with 5% MeOH/CH2Cl2 afforded the title compound.

Workup

additionAfter the addition
temperature, cooled
customthe solvent removed under reduced pressure
dissolutionThe residue was dissolved in chloroform (35 ml)
extractionthe solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml)
dry with materialdried (sodium sulphate)
customEvaporation of the solvent and purification of the residue by silica column chromatography
washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-69934a33dc154cb08ca603e0313609a4
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198539

Reaction notes

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