Water → HCID 68745073, compound

Participants

Reaction Steps

To a solution of 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-chloro-1-[4-(2-hydroxyethyl)benzyl]-1H-indole (0.13 g) in N,N-dimethylformamide (3 mL) was added 55% sodium hydride (9 mg) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added a solution of methyl iodide (0.020 mL) in tetra hydrofuran (1 mL) at the same temperature, and the mixture was stirred at the same temperature for 15 minutes, and stirred at room temperature for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1) to give 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-chloro-1-[4-(2-methoxy-ethyl)benzyl]-1H-indole (0.13 g). This material was dissolved in a mixed solvent of methanol (1 mL) and ethyl acetate (4 mL). To the solution was added 10% palladium-carbon powder (60 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 30 minutes. To the reaction mixture was added sodium hydrogen carbonate (200 mg), and the mixture was stirred at room temperature for 10 minutes. The insoluble material was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK C18 ODS, UG80, 5 μm, 20×50 mm, linear gradient water/methanol=90/10-10/90, flow rate 30 mL/min) to give the title compound (39 mg).

Provenance & Evidence