1-Hydroxybenzotriazole → HCID 178472752, compound

Participants

Reaction Steps

To a stirred solution of 5-(3-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid (1 g, 0.00340 mol) in DMF (5 mL) was added DIPEA (1.976 g, 0.01529 mol), HOBt (0.574 g, 0.00425 mol) and EDCI.HCl (0.814 g, 0.00425 mol) at ambient temperature. After 5 minutes glycine ethyl ester hydrochloride (0.498 g, 0.00357 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried. The crude product was recrystallized from ethyl acetate to afford 0.54 g (36%) of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid ethyl ester. LCMS: 380.15 (M+1)+, 92.05%. To a stirred solution of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid ethyl ester (0.54 g, 0.00136 mmol) in a mixture of THF (50 mL), methanol (25 mL) and H2O (25 mL) was added LiOH.H2O (0.18 g, 0.0042 mol) at ambient temperature. The resulting mixture was stirred at ambient temperature overnight. Volatiles were removed by evaporation and the resulting residue was diluted with water, acidified with concentrated HCl solution. The resulting precipitate was isolated by filtration and dried afford 0.44 g (92%) of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid. LCMS: 352.12 (M+1)+, 97.85%,

Provenance & Evidence