Ammonia → HCID 12016015, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aS, 4S, 6R, 6aR)-6-benzyloxy-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (588.6 mg, 2 mmol) in methanol (8.8 mL) was added methanesulfonic acid (0.007 mL, 0.1 mmol), and the mixture was stirred with heating to 60° C. for 24 hours. After the solution was dried under reduced pressure, ethyl acetate (2.9 mL) and 2,2-dimethoxypropane (0.17 mL, 1.4 mmoL) were added to the resulting oil, and the mixture was stirring at ambient temperature for 2 hours. Aqueous 7% sodium hydrogen carbonate solution (0.5 mL) was added for layer separation, and the resulting organic layer was concentrated under reduced pressure, to which was added aqueous 28% ammonia (1.2 mL, 20 mmol), and the mixture was stirred at ambient temperature for 14 hours. To the resulting solution was added ethyl acetate (3 mL) for layer separation, and the organic layer was concentrated under reduced pressure. To the resulting solid was added a hexane/ethyl acetate (3:1) solution (3 mL) for rinsing as a slurry at ambient temperature for 2 hours. Subsequently, the solid was filtered and rinsed in a hexane/ethyl acetate (3:1) solution (0.5 mL). The solid was dried under reduced pressure to recover (3aS, 4S, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxol-4-carboxylic acid amide (278.7 mg; yield of 64.2%) as a white solid. Melting point: 136° C.

Provenance & Evidence