Chloroform → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was prepared as follows. 2-Acetamido-2-deoxy-D-glucose (50 g, 0.226 mol) was added to chilled acetyl chloride (125 ml). The mixture was then stirred at room temperature for 16 hr. Chloroform (300 ml) was added to the reaction mixture through the condenser and the resulting homogeneous solution was added to a vigorously stirred solution of 400 grams of ice and 100 ml of water. The organic layer was separated, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. This filtrate was concentrated to about 75 ml under reduced pressure. Ether (400 ml) was added to the concentrated solution and left at room temperature for 2 hr to give the product as a white solid. This white solid was filtered and dried in a vacuum desiccator over sodium hydroxide and phosphorous pentoxide to give 52.5 grams of the title cmp. M.p. 123°-125° C.

1. customThe organic layer was separated
2. washwashed with saturated sodium bicarbonate
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationThis filtrate was concentrated to about 75 ml under reduced pressure
6. additionEther (400 ml) was added to the concentrated solution
7. waitleft at room temperature for 2 hr

ORD record

ord-76fe81f4e0b94f5cbde953ffa572c2e6

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091523