Pivaloyl chloride → HCID 18648374, compound

Participants

Reaction Steps

To a stirred solution of 2',3'-dideoxy-5-ethynyl-3'-fluorouridine (0.106 g 0.4 mmol) in dry pyridine (5 ml) at 0° C. was added trimethylacetyl chloride (0.06 ml, 0.48 mmol) and stirring continued at 0° C. for 1.5 hours. After stirring at room temperature for 24 hours, a further aliquot of the acid chloride (0.03 ml, 0.24 mmol) was added and stirring maintained for a further 3 hours. After quenching with methanol (3 ml), the solvent was removed by evaporation under reduced pressure and co-evaporated with several portions of ethanol (2×30 ml) and the resulting oil was chromatrographed on a silica gel column eluting with 5% MeOH/CH2Cl2. The appropriate fractions were combined and evaporated to dryness and the residue was recrystallised twice from ethanol to give the chromatographically pure title product.

Provenance & Evidence