Diphenyl carbonate → HCID 117599832, compound

Participants

Reaction Conditions

Reaction Steps

The benzyloxy protected 4′-fluorouridine (A3, 2.8 g, 7.6 mmol) was dissolved in DMF (10 mL). Solid diphenylcarbonate (1.80 g, 8.42 mmol, 1.1 eq) was added followed by solid sodium bicarbonate (0.36 g, 4.56 mmol 0.6 eq). The mixture was stirred and heated to 110° C. under an argon atmosphere for 8.5 hours at which time the reaction was shown to be complete by tlc (silica gel, EtOAc:MeOH=4:1). The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in methanol, and was purified by CombiFlash® column chromatography (Silica gel; 0 to 100% EtOAc:Heptane to 2:1 EtOAc:MeOH) providing the desired material in 68% yield (A4, 1.8 g).

Provenance & Evidence