Ammonium Chloride → 4-({4-[(1E)-3-Carbamoylprop-1-enyl]phenyl}methyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

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Reaction Steps

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole (32 mg) in N,N-dimethylformamide (1 mL) were added ammonium chloride (8 mg), 1-hydroxybenzotriazole (9 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15 mg) and triethylamine (21 mg), and the mixture was stirred at room temperature overnight. The insoluble material was removed by filtration, 5 mol/L aqueous sodium hydroxide solution (0.5 mL) was added to the filtrate, and the resulting mixture was stirred at room temperature for 1 hour. The insoluble material was removed by filtration, and the filtrate was purified by preparative reverse phase column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL/minute linear gradient, water/acetonitrile=90/10-10/90) to give the title compound (7 mg).

Provenance & Evidence