p-Anisoyl chloride → HCID 53936791, compound

HRID 728204Notes

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[S:23][CH:24]=[CH:25][CH:26]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1>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:40](=[O:41])[C:39]3[CH:43]=[CH:44][C:36]([O:35][CH3:34])=[CH:37][CH:38]=3)[C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][CH2:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.30 g of 5'-O-acetyl-2'-deoxy-5-fluoro-3'-O-(2-thienyl)methyluridine in 10 ml of dioxane were added 0.55 ml of triethylamine and 0.16 g of 4-methoxy-benzoyl chloride. The mixture was stirred at 80° C. for 2 hours. The solvent was distilled off and the residue was dissolved in 30 ml of ethyl acetate. The solution was washed with water. The ethyl acetate layer was dried over sodium anhydrous sulfate and concentrated. The residue was subjected to silica gel chromatography and purified by elution with chloroform, giving 0.37 g of 5'-O-acetyl-2'-deoxy-5-fluoro-3-(4-methoxybenzoyl)-3'-O-(2-thienyl)me thyluridine in a yield of 91%.

Workup

distillationThe solvent was distilled off
dissolutionthe residue was dissolved in 30 ml of ethyl acetate
washThe solution was washed with water
dry with materialThe ethyl acetate layer was dried over sodium anhydrous sulfate
concentrationconcentrated
custompurified by elution with chloroform

Sources & evidence

ORD record: ord-4c2a669e7f30480b8bdb0e783962982f
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047521

Reaction notes

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