Hydrochloric Acid → HCID 19077439, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.036 ml, 0.41 mmol) in dichloromethane (3 ml) -78° C. was added dimethylsulfoxide (0.063 ml, 0.82 mmol), and over 5 minutes, 1-(10-hydroxyeicosyl)-3,7-dimethylxanthine (0.135 g, 0.28 mmol) in dichloromethane (2 ml). The reaction was stirred at -78° C. for 30 minutes and after the addition of triethylamine (0.23 ml, 1.64 mmol) allowed to warm to 25° C. over 30 minutes. Hydrochloric acid (1.0M, 10 ml) and dichloromethane (5 ml) were added, the organic phase separated and the aqueous phase washed with dichloromethane (10 ml). The organic portions were combine and dried over magnesium sulfate. Evaporating the solvent left a slightly yellow solid, which upon purification by chromatography (silica, ethyl acetate) produced 0.110 g of 1-(10-oxoeicosyl)-3,7-dimethylxanthine as a white solid (85% yield).

Provenance & Evidence