1-Hydroxybenzotriazole → HCID 87558202, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-[4-((1E)-3-carboxyprop-1-enyl)benzyl]-7-methyl-1H-indole (0.10 g), 1-(2-amino-2-methylpropionyl)-4-isopropylpiperazine (31 mg), 1-hydroxybenzotriazole (18 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (35 mg) and triethylamine (0.034 mL) in N,N-dimethylformamide (2 mL) was stirred at 50° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with an aqueous potassium carbonate solution 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: dichloromethane/methanol=20/1-12/1) to give 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-[4-((1E)-3-{1-[(4-isopropylpiperazin-1-yl)carbonyl]-1-(methyl)ethylcarbamoyl}prop-1-enyl)benzyl]-7-methyl-1H-indole (0.11 g). This material was dissolved in a mixed solvent of methanol (3 mL) and tetra hydrofuran (3 mL). To the solution was added 10% palladium-carbon powder (0.50 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours. The insoluble material was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1-3/1) to give the title compound (19 mg).

Provenance & Evidence