Ammonia → HCID 22822365, compound

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.).

1. customwell closed
2. customThe mixture was evaporated to dryness in vacuo
3. additionThe residue was mixed with a small amount of ethyl acetate
4. customchromatographed on a column of silica gel (2.54×20 cm)
5. concentrationThe methanol effluent was concentrated to ca. 75 ml
6. addition, and ethyl acetate (500 ml.) was added
7. customto give a precipitate
8. filtrationThe creamy yellow precipitate was filtered
9. customdried at room temperature in vacuo
10. customyielding 2.77 g

ORD record

ord-afcfab2580c94227b1395dc2658ad7a3

Source dataset

uspto-grants-1983_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04367226