Benzene → HCID 131714688, compound

Participants

Reaction Steps

A solution of β-phenylethyl 6-(1-methyl-2-methoxyethylamino)-6-deoxy-α-D-altropyranoside (6.65 g, 18.7 mmol) in a mixture of methanol (30 ml), dioxane (20 ml), and benzene (10 ml) was dropped into a solution of p-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (5.64 g, 20.6 mmol) in a mixture of acetone (50 ml) and isopropyl ether (20 ml) with well stirring at 0° to 5° C. spending 5 minutes, and reaction was continued for further 2 hours at the same temperature. After confirmation by TLC that the reaction was finished, the reaction mixture was vacuum-concentrated at 25° C. and fractionated by column chromatography (packing: Kiesel gel 60; eluent: chloroform→chloroform/methanol 39:1) to separate the objective product of α-form. The objective fractionated solution was vacuum-concentrated at 25° C. and crystallized from methanol and water, giving 6.03 g of 3-(1-methyl-2-methoxyethyl)-3-(β-phenylethyl α-D-altropyranose-6-yl)-1-(2-chloroethyl)-1 -nitrosourea; yield 65.8%, m.p. 55°-57° C., [α]D20 +17.8° (C 1.0, methanol).

Provenance & Evidence