Succinic Acid → HCID 131711518, compound

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Reaction Steps

2.35 g (10 mmol) of n-butyl 6-amino-6-deoxy-α-D-glucopyranoside is dissolved in a mixture of 50 ml isopropanol and 50 ml dimethylformamide, and to this solution is added succinic acid powder, with stirring, to adjust the PH of the solution to 9.1. The resulting solution is then added dropwise to a solution prepared by dissolving 3.17 g (12.5 mmol) of o-cyanophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 20 ml tetrahydrofuran and 10 ml benzene, while stirring, at 0°-10° C. over 30 minutes. The resultant mixture is stirred at the same temperature for a further 2 hours, and thus reacted solution is, after filtering, 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 3.13 g of 3-(n-butyl α-D-glucopyranos-6-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 84.6%. mp 108°-109° C. (decomp.). [α]D25 +147° (C 0.5, water). Analysis for C13H24N3O7Cl (MW 369.80):

Provenance & Evidence