1,3-Benzodioxole-5-carboxylic acid → HCID 53839260, compound

Participants

Reaction Steps

A solution of piperonylic acid (0.42 g) in dry acetonitrile (5 ml) containing triethylamine (0.36 ml) was treated with diethyl chlorophosphate (0.37 ml) for 1 hour. To the reaction mixture were added 2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5-fluorocytidine (1.0 g) obtained in Reference example (a), triethylamine (0.36 ml) and 4-dimethylaminopyridine (0.05 g). After stirring of the mixture for 12 hours at room temperature, acetonitrile was evaporated under reduced pressure. The residue was partitioned between water and ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained powder was dissolved in tetrahydrofuran (6.3 ml) containing tetrabutylammonium fluoride (1.65 g) and the reaction mixture was stirred for 1 hour. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (isopropanol-dichloromethane) followed by recrystallization from ethyl acetate to give 0.5 g of 5'-deoxy-5-fluoro-N4 -piperonyloylcytidine, mp 124°~125° C.: MS 394 (MH+).

Provenance & Evidence