Phenethylamine → HCID 57695524, compound

Participants

Reaction Steps

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid (965 mg, 2 mmol) was dissolved in DMF (anhydrous, 10 ml), and CDI (324 mg, 2 mmol) was added and the resulting solution was stirred at r.t for 2 h. 2-Phenethylamine (267 mg, 2.2 mmol) solution in DMF (5 ml) was added and the resulting solution was stirred at r.t. until the reaction was complete. The reaction was diluted with water (50 ml), extracted with dichloromethane (50 ml×3), and the combined organics were washed thoroughly with water to remove DMF and dried over sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid phenethyl-amide (1101 mg, 94%). M.p.: 138-140° C.; 400 MHz 1H NMR (CDCl3) δ: 8.17 (s, 1H), 7.87 (t, J=5.6 Hz, 1H), 7.40-7.36 (m, 3H), 7.32-7.11 (m, 14H), 6.87 (d, J=8.0 Hz, 1H), 6.54 (s, 1H), 5.03 (s, 2H), 5.00 (s, 2H), 3.72 (s, 3H), 3.64 (q, J=6.4 Hz, 2H), 2.92-2.81 (m, 1H), 2.75 (t, J=7.2 Hz, 2H), 1.23 (d, J=7.2 Hz, 6H); LCMS: 586 [M+H].

Provenance & Evidence