Benzoyl chloride → HCID 117793648, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of chiral 1-((2R,3R,4R)-3-fluoro-4-hydroxy-3-methyl-5-methylene-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (18.3 g, 75.6 mmol) and DMAP (27.7 g, 227 mmol) in anhydrous THF (900 mL) at 0° C. was added BzCl (15.9 g, 113.4 mmol) dropwise. The reaction mixture was stirred at 0° C. for 0.5 h, then sat. NaHCO3 was added to quench the reaction. The mixture was extracted with EA (300 mL×3). The combined organic extract was washed with H2O, brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography column (DCM:MeOH=160:1 to 120:1) to give the title compound as a white solid (17 g, 65%).

Provenance & Evidence