HCID 14158562, compound → HCID 14187546, compound

997.2 mg (3.31 mmol) of 2,3,4-tri-O-acetyl-β-L-xylopyranosyl azide was dissolved in 30 ml of methanol, and the solution was allowed to react at 45° to 50° C. for 2 hours in a hydrogen gas stream in the presence of 300 mg of 5% palladium carbon catalyst. The reaction solution was then filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 60 ml of pyridine, and 10 ml of acetic anhydride was added. The mixture was allowed to react at room temperature for 4 hours. The reaction mixture was then concentrated under reduced pressure and the residue extracted with chloroform (100 ml). The chloroform layer was washed with 2N aqueous hydrochloric acid solution (100 ml), 10% aqueous sodium carbonate solution (100 ml) and water in the stated order, dehydrated over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (Waggle C-200, 30 g) and eluted with chloroform-methanol (300:1). The eluate was crystallized from ethyl acetate-hexane to obtain 309.9 mg (0.98 mmol, 30%) of 2,3,4-tri-O-acetyl-β-L-xylopyranosylamine as a colorless needle crystal. The physicochemical properties of this crystalline compound were as follows.

1. filtrationThe reaction solution was then filtered
2. concentrationthe filtrate concentrated under reduced pressure
3. dissolutionThe residue was dissolved in 60 ml of pyridine
4. addition10 ml of acetic anhydride was added
5. customto react at room temperature for 4 hours
6. concentrationThe reaction mixture was then concentrated under reduced pressure
7. extractionthe residue extracted with chloroform (100 ml)
8. washThe chloroform layer was washed with 2N aqueous hydrochloric acid solution (100 ml), 10% aqueous sodium carbonate solution (100 ml) and water in the stated order
9. concentrationconcentrated under reduced pressure
10. washeluted with chloroform-methanol (300:1)
11. customThe eluate was crystallized from ethyl acetate-hexane

ORD record

ord-4ba6538f270e4902b4354fd37d7f857e

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04959460