1-Hydroxybenzotriazole → HCID 86699107, compound

Participants

Reaction Steps

To a stirred solution of N-[(benzyloxy)carbonyl]-2-methylalanine (Preparation 56, 35 g, 0.15 mmol) in DCM (600 mL) was added HOBt (25 g, 0.18 mmol) followed by EDCI.HCl (35.5 g, 0.18 mmol) and the reaction stirred at room temperature for 30 minutes. 4-Bromobenzene-1,2-diamine (30.7 g, 0.16 mmol) was added and the reaction heated to reflux for 24 hours. The reaction was cooled and poured into water (500 mL). The organic layer was separated, washed with water (200 mL), brine (100 mL) dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography to afford the title compound as a brown solid that was taken directly on to the next step (80 g, 66%).

Provenance & Evidence