Ammonia → HCID 22822365, compound

Participants

Reaction Steps

Ethyl 2-(N-β-D-glucopyranosyl)aminothiazole-4-carboxylate hydrobromide (4.15 g., 0.01 mole) was added to a solution of methanol (50 ml.) saturated with ammonia at 0° in a pressure bottle. The reaction mixture was magnetically stirred at room temperature for 48 hours with the stopper well closed. The mixture was evaporated to dryness in vacuo. The residue was mixed with a small amount of ethyl acetate and chromatographed on a column of silica gel (2.54×20 cm) using acetone as the first solvent (300 ml.) and methanol as the second solvent (300 ml.). The methanol effluent was concentrated to ca. 75 ml., and ethyl acetate (500 ml.) was added to give a precipitate. The creamy yellow precipitate was filtered and dried at room temperature in vacuo, yielding 2.77 g. (76.2%); m.p. over 96° (dec.).

Provenance & Evidence