Hydrochloric Acid → 3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-5-isopropyl-4-({4-[3-(methanesulfonyloxy)-propoxy]phenyl}methyl)-1H-pyrazole

Participants

Reaction Steps

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole (2.21 g) in dichloromethane (35 mL) were added triethylamine (0.65 mL) and methanesulfonyl chloride (0.33 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethylacetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-isopropyl-4-({4-[3-(methanesulfonyloxy)propoxy]phenyl)methyl}-1H-pyrazole. This material was dissolved in N,N-dimethylformamide (20 mL). To the solution was added sodium azide (0.46 g), and the mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethylacetate. The organic layer was washed with water three times, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate 1/1-1/3) to give the title compound (1.6 g).

Provenance & Evidence