N-Hydroxysuccinimide → HCID 57824469, compound

Participants

Reaction Steps

To a stirred solution of 2,3,4-tri-O-methyl-L-rhamnose (6.5 g, 31.5 mmol) and N-hydroxysuccinimide (5.4 g, 47 mmol) in benzene (50 mL) was added p-toluenesulfonic acid (50 mg, cat.). The solution was heated to reflux and water (H2O) was collected using a Dean-Stark trap. After 4 h, the solution was cooled and the supernatant toluene layer was separated from a small amount of insoluble gum. The organic layer was washed with a saturated solution of sodium bicarbonate (NaHCO3; 20 mL), then dried over MgSO4 and concentrated to a solid. Recrystallization from ether (Et2O)-hexanes gave the title compound (4.95 g, 52%) as an off-white solid.

Provenance & Evidence