Carbon Dioxide → HCID 131711518, compound

Participants

Reaction Steps

2.35 g (10 mmol) of n-butyl 6-amino-6-deoxy-α-D-glucopyranoside is dissolved in a mixture of 25 ml methanol and 25 ml tetrahydrofuran, and to this solution is added 4.40 g (100 mmol) of dry-ice little by little so as to convert said glucopyranoside into its carbonic acid-addition salt. This acid-addition salt solution is then added dropwise to a solution, which has been prepared by dissolving 3.04 g (12 mmol) of o-cyanophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 13 ml tetrahydrofuran and 13 ml isopropyl ether and which has been cooled to 0°-5° C., while stirring, over 20 minutes. The resultant mixture is stirred further at 22°-25° C. for 2 hours. The thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with n-hexane and then with ethyl ether, dried under reduced pressure, and recrystallized from isopropanol to give 3.2 g of 3-(n-butyl α-D-glucopyranos-6 -yl)-1-(2-chloroethyl)-1-nitrosourea as pale yellowish crystals. Yield 86.5%. mp 107°-109° C. (decomp.). [α]D25 +147° (C 0.5, methanol). Analysis for C18H24N3O7Cl (MW 369.80):

Provenance & Evidence