Water → HCID 131714694, compound

Participants

Reaction Steps

2-Chloroethyl isocyanate (1.33 g) and barium carbonate (2.5 g) were added to a solution of n-butyl 6-(3-methoxy-n-propylamino)-6-deoxy-D-glucopyranoside 1/2 sulfate (3.64 g, 10.5 mmol) in a mixture of water (10 ml) and methanol (30 ml) at 0° to 5° C., and the mixture was heated under reflux on a water bath for 1 hour. The reaction mixture was then filtered while hot, to remove the insoluble barium salt. The filtrate was vacuum-concentrated and fractionated by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1) to separate the α- and β-form of products. The objective α- and β-form product fractions were each vacuum-concentrated at 25° C. and crystallized from aqueous isopropanol, giving 1.40 g of 3-(3-methoxy-n-propyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-urea; yield 32.2%, m.p. 103°-105° C., [α]D20 +50.8° (C 1.0, methanol); and 1.32 g of 3-(3-methoxy-n-propyl)-3-(n-butyl β-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea; yield 30.4%, m.p. 109°-111° C., [α]D20 -4.7° (C 1.0, methanol).

Provenance & Evidence