1-Hydroxybenzotriazole → HCID 57912296, compound

Participants

Reaction Steps

HBTU (183 mg, 0.482 mmol) and HOBt (65.1 mg, 0.482 mmol) were added to a stirring solution of Compound 10 (150 mg, 0.482 mmol) in anhydrous DMF (4.82 mL) followed by N,N-diisopropylethylamine (187 mg, 1.45 mmol) and propargyl amine (79.6 mg, 1.45 mmol). The resulting solution was stirred for 30 h at room temperature after which time 25 mL of EtOAc were added and the solution was washed with water (3×10 mL), aqueous saturated NH4Cl (1×10 mL), and brine (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated on a rotary evaporator. The resulting oil was purified by silica gel chromatography (50% EtOAc:hexanes) to yield Compound 11 as a white solid (92.3 mg, 55%).

Provenance & Evidence