Carbon Dioxide → 2-[3-(2-Chloroethyl)-3-nitrosoureido]-D-glucopyranose

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Reaction Steps

1.79 g (10 mmol) of 2-amino-2-deoxy-D-glucopyranose is dissolved in a mixture of 20 ml anhydrous methanol and 10 ml dimethylformamide, and the solution is cooled to 0°-5° C. To this solution is added 2.2 g (50 mmol) of dry-ice little by little so as to convert said glucopyranose into its carbonic acid-addition salt. This acid-addition salt solution is then added dropwise to a solution prepared by dissolving 3.04 g (12 mmol) of o-cyanophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 20 ml anhydrous tetrahydrofuran and 10 ml methylene chloride, while stirring, at 0°-5° C. over an hour. The resultant mixture is stirred further at 22°-25° C. for 2 hours, and the thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with petroleum ether, dried under reduced pressure, and recrystallized from anhydrous ethanol to give 2.58 g of 3-(D-glucopyranos-2-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 82.2%. mp 147°-148° C. (decomp.). Analysis for C9H16N3O7Cl (MW 313.69):

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