Propylamine → HCID 86653783, compound

Participants

Reaction Steps

A solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanoic acid (325 mg) in 3 mL THF was treated with carbonyldiimidazole (177 mg, 1.06 mmol). The cloudy yellow solution was stirred at room temperature for 1.5 h. One portion of ˜0.45 mmol was added to a solution of n-propylamine (155 μL, 111 mg) in 2 mL THF and let stir overnight. The reaction mixture was concentrated to a pink-tan solid, dissolved into 5 mL CH2Cl2 and washed with 1×3 mL 2.5 M HCl, 1×3 mL saturated aqueous NaHCO3, 2×2 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to yield 117 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-N-propylbutanamide as a white powder. MS M++H at 460 m/z; 1H NMR (400 MHz, CDCl3) δ=7.50 (m, 4 H), 7.44-7.35 (m, 6 H), 5.47 (br m, 1 H), 4.74 (s, 2 H), 4.73 (s, 2 H), 3.03 (q, 2 H), 2.70 (t, 2 H), 2.27 (s, 3 H), 2.25 (s, 3 H), 2.23 (s, 3 H), 2.14 (t, 2 H), 1.84 (pent, 2 H), 1.39 (m, 2 H), 0.84 (t, 3 H) ppm.

Provenance & Evidence