Benzilic acid → HCID 10324628, compound

Participants

Reaction Steps

A mixture of hydroxy(diphenyl)acetic acid (100 mg, 0.44 mmol) and 1,1′-carbonyldiimidazole (78 mg, 0.48 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 3 h, then a solution of N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methyl propanamide (140 mg, 0.44 mmol) in CH2Cl2 (5 mL) was added. The resulting mixture was stirred at room temperature for overnight, evaporated in vacuo, and dissolved in a mixture of EtOAc and 1N NaOH. The organic layer was separated, washed twice with water, dried over MgSO4 and concentrated. The residue was purified over preparative TLC (10% 2M NH3/MeOH in 50% EtOAc/hexane) to give 111 mg (0.21 mmol, 48%) of (N-{3-[1-(3-{[hydroxy(diphenyl)acetyl]amino}propyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide: 1H NMR (400 MHz, CDCl3) δ 9.22 (s, 1 H), 8.14 (s, 1 H), 7.80 (s, 1 H), 7.64–7.48 (m, 4 H), 7.32–7.16 (m, 6 H), 6.95 (d, 1 H, J=8.0 Hz), 6.64 (d, 1 H, J=8.0 Hz), 5.83–5.62 (br, 1 H), 3.54–3.38 (m, 2 H), 3.11–2.94 (m, 2 H), 2.79–2.59 (m, 1 H), 2.57–2.41 (m, 2 H), 2.26 (s, 3 H), 2.29–2.16 (m, 1 H), 2.16–1.91 (m, 4 H), 1.74–1.53 (m, 4 H), 0.86 (d, 6 H, J=6.8 Hz); ESMS m/e: 528.4 (M+H)+.

Provenance & Evidence