Triethylamine → HCID 131723446, compound

Participants

Reaction Steps

A cold (0° C.) solution of N-Boc-D-homophenylalanine (300 mg) in dichloromethane (10 mL), under nitrogen atmosphere, was treated sequentially with triethylamine (165 μL) and ethyl chloroformate (102 μL). After stirring for 2 h at 0 C, the crude mixed anhydride was added dropwise to a solution of L-serine ethyl ester hydrochloride (182 mg), triethylamine (300 μL), and dichloromethane (2 mL). The mixture is stirred at 0° C. for 1 h and then allowed to warn to 25° C. and stirred for 12 h. The reaction mixture is diluted with ethyl acetate, washed successively with water and brine, dried (Na2SO4) and concentrated. The residue was purified using chromatography over silica gel (50% ethyl acetate/hexane) to afford the title compound (371 mg): 1H NMR (400 MHz, CDCl3) δ 1.32 (t, J=9.8 Hz, 3H), 1.46 (s, 9H), 1.97 (m, 1H), 2.11 (m, 1H), 2.75 (t, J=10.4 Hz, 2H), 3.97 (m, 2H), 4.14 (m, 1H), 4.25 (q, J=9.8 Hz, 2H), 4.60 (m, 1H), and 7.18-7.29 (m, 5H).

Provenance & Evidence