1-Hydroxybenzotriazole → 4-[2-(Biphenyl-4-ylcarbamoyl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

HOBt (570 mg, 4.2 mmol) and DIPEA (541 mg, 4.2 mmol) were added to a stirred solution of N-biphenyl-4-yl-malonamic acid (1 g, 3.5 mmol) in DMF (10 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (810 mg, 4.2 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (720 mg, 3.86 mmol) were added. The resulting reaction mixture was stirred at room temperature overnight. Water was then added and the resulting precipitate was filtered and dried to afford 1.4 g (93%) of 4-[2-(biphenyl-4-ylcarbamoyl)-acetyl]-piperazine-1-carboxylic acid tert-butyl ester. 1H NMR: (CDCl3): δ 8.6 (s, 1H), 7.9 (m, 2H), 7.7 (m, 2H), 7.65 (m, 1H), 7.5 (m, 3H), 7.4 (s, 1H), 4.1 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.1 (m, 2H).

Provenance & Evidence