Water → HCID 9815399, compound

Temperature

100 °C

A solution of 16 mg of powdery 2-amino-4-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]oxazole-4,5,6-triol dissolved in 2 ml of 6N aqueous hydrochloric acid was sealed in an ampoule and then hydrolyzed by heating at 100° C. for 24 hours. At the end of this time, water was added to the hydrolyzate, and the resulting mixture was concentrated to dryness by evaporation under reduced pressure. The residue was again dissolved in water, and the resulting solution was again concentrated to dryness, to remove the hydrochloric acid, and then the resulting residue was dissolved in 20 ml of water and the pH of the solution was adjusted to a value of 6.0 by the addition of a 1N aqueous solution of sodium hydroxide. The solution was passed through 20 ml of Amberlite CG-50 (NH4+) to hold the 5-amino-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol by adsorption, and the column was washed with 60 ml of deionized water and then eluted with a 0.2N aqueous ammonia solution. The eluate was concentrated by evaporation under reduced pressure, to yield 5 ml of a concentrate. This concentrate was placed on a column packed with 50 ml of Dowex 1X2 (OH-), and the column was washed with 200 ml of deionized water and then eluted with 20% v/v aqueous methanol. The eluate was fractionated in 5 ml portions. Fractions 5-23, which exhibited an inhibitory activity against β-glucosidase were combined and concentrated by evaporation under reduced pressure. The concentrate was lyophilized to give 6.2 mg of 5-amino-1-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol as a colorless powder having the properties described hereinabove.

1. customwas sealed in an ampoule
2. concentrationthe resulting mixture was concentrated to dryness by evaporation under reduced pressure
3. dissolutionThe residue was again dissolved in water
4. concentrationthe resulting solution was again concentrated to dryness
5. customto remove the hydrochloric acid
6. dissolutionthe resulting residue was dissolved in 20 ml of water
7. additionthe pH of the solution was adjusted to a value of 6.0 by the addition of a 1N aqueous solution of sodium hydroxide
8. washthe column was washed with 60 ml of deionized water
9. washeluted with a 0.2N aqueous ammonia solution
10. concentrationThe eluate was concentrated by evaporation under reduced pressure
11. customto yield 5 ml of a concentrate
12. washthe column was washed with 200 ml of deionized water
13. washeluted with 20% v/v aqueous methanol
14. concentrationconcentrated by evaporation under reduced pressure

ORD record

ord-5d83e0acc0154851b8208890295c508c

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05260447