Benzyloxycarbonylglycine → HCID 68942621, compound

Participants

Reaction Steps

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole (0.1 g) in N,N-dimethylformamide (1 mL) were added 2-benzyloxycarbonylaminoacetic acid (51 mg), 1-hydroxybenzotriazole (33 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (93 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate-dichloromethane/methanol=30/1-20/1) to give 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-{3-[2-(benzyloxycarbonylamino)acetylamino]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole (46 mg). This material was dissolved in methanol (3 mL). To the solution was added 10% palladium-carbon powder (20 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1.5 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[3-(2-aminoacetylamino)propoxy]phenyl}methyl)-5-isopropyl-1H-pyrazole (34 mg). This material was dissolved in methanol (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.01 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (23 mg).

Provenance & Evidence