Glucopyranosylamine → N-(2-Chloroethyl)-N'-beta-D-glucopyranosyl-N-nitrosourea

3.28 g (12 mmol) of o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate is dissolved in a mixture of 10 ml anhydrous dimethylformamide and 10 ml anhydrous ethanol, and to this solution is added little by little 1.79 g (10 mmol) of 1-amino-1-deoxy-β-D-glucopyranose powder, while stirring, at 5°-10° C. over 10 minutes. The resultant mixture is, after adding 5 ml of anhydrous dimethylformamide thereto, stirred further at 10° C. for 5 hours, and the thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with anhydrous ethyl ether and then with acetone, dried under reduced pressure, and recrystallized from anhydrous ethanol-ethyl ether (1:5) to give 2.47 g of 3-(β-D-glucopyranosyl)-1-(2-chloroethyl)-1-nitrosourea. Yield 78.7%. mp 77°-78° C. (decomp.). [α]D25 -10.3° (C 1.0, water). Analysis for C9H16N3O7Cl (MW 313.69):

1. stirringstirred further at 10° C. for 5 hours
2. concentrationthe thus reacted solution is concentrated at 40° C.
3. customThe crystalline residue obtained
4. washis washed with anhydrous ethyl ether
5. dry with materialwith acetone, dried under reduced pressure
6. customrecrystallized from anhydrous ethanol-ethyl ether (1:5)

ORD record

ord-f0f3b5deda30497dba7e23e56403c61f

Source dataset

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04156777