Acetic Anhydride → HCID 20773484, compound

Participants

Reaction Steps

To a stirred solution of (R)-8-benzyloxymethyl-1-(5-hydroxyhexyl)-3-methylxanthine (19.9 g, 51.5 mmol), triethylamine (10.4 g, 103 mmol) and 4-dimethylaminopyridine (1.33 g, 11 mmol) in chloroform (130 ml) was added acetic anhydride (6.57 g, 64.4 mmol). After stirring for 3 hours at room temperature, the reaction mixture was quenched by addition of methanol (5 ml). The mixture was washed with aqueous potassium hydrogen sulfate solution (0.1 N) to pH 6-7, with water (2×50 ml) and with saturated aqueous sodium chloride solution (50 ml). After drying over magnesium sulfate, the organic solution was evaporated under reduced pressure to provide (R)-1-(5-acetoxyhexyl)-8-benzoxymethyl-3-methylxanthine (19.6 g, 88% yield) as white colored solid.

Provenance & Evidence