Dimethylformamide → 4-[2-(4-Benzyloxy-benzoylamino)-acetyl]-piperazine-1-carboxylic acid o-tolylamide

Participants

Reaction Steps

DIPEA (136 mg, 0.182 mL, 1.05 mmol) was added to a stirred solution of (4-Benzyloxy-benzoylamino)-acetic acid (100 mg, 0.35 mmol) in DMF (1 mL). HOBT (57 mg, 0.42 mmol) and EDCI.HCl (83 mg, 0.42 mmol) were added at room temperature. After 2 minutes piperazine-1-carboxylic acid O-tolylamide TFA salt (140 mg, 0.42 mmol) was added. The reaction mixture was diluted with cold water and the resulting precipitate was filtered under reduced pressure to afford 87 mg (50.8% yield) of 4-[2-(4-benzyloxy-benzoylamino)-acetyl]-piperazine-1-carboxylic acid o-tolylamide. LCMS Purity %: 89.31, HPLC Purity %: 91.55, 1H NMR (DMSO-d6): δ 8.5-8.4 (bt, 1H), 8.2-8.1 (s, 1H), 7.9-7.8 (d, 2H), 7.4 (m, 5H), 7.2-7.0 (m, 6H) 5.2 (s, 2H), 4.2-4.1 (d, 2H), 3.5 (m, 8H), 2.2 (s, 3H).

Provenance & Evidence