Triethylamine → HCID 69891013, compound

Participants

Reaction Steps

A mixture of phenylpropiolic acid (10 g, 68.4 mmol) and thionyl chloride (6 mL, 76.6 mmol) in Et2O (50 mL) was stirred overnight at room temperature. The resulting mixture was concentrated under reduced pressure, then diluted with THF (100 mL). This acid chloride solution was added to a 0° C. solution of ethyl 2-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetate (15 g, 63.2 mmol) and Et3N (22 mL, 156 mmol) in THF (250 mL) dropwise over 25 min. The reaction mixture was allowed to warm to room temperature, stirred for 1.5 h, then treated with water and extracted with EtOAc. The organic layer was washed with a 1N HCl solution, water, a saturated NaHCO3 solution and a saturated NaCl solution. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give ethyl 2-{N-[(1S)-1-(4-methoxyphenyl)ethyl]-3-phenylprop-2-ynoylamino}acetate (18.9 g, 82%) as a slightly yellow oil: TLC (40% EtOAc/hex) Rf 0.40; 1H NMR (CDCl3) δ 1.14-1.33 (m, 3H), 1.66 (d, J=7.0 Hz, 3H), 3.82 (s, 3H), 4.06-4.21 (m, 4H), 5.59 (q, J=7.4 Hz, 0.6H), 6.03 (q, J=7.4 Hz, 0.4H), 6.86-6.93 (m, 2H), 7.25-7.61 (m, 7H); HPLC ES-MS m/z (rel abundance) 388 (MH+, 100%).

Provenance & Evidence