Triethylamine → (R)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Participants

Reaction Steps

Following general method B, to a solution of A1 (55.33 mg, 0.25 mmol) in dry dichloromethane (2 mL) at 0° C. was added triethylamine (0.043 mL, 0.28 mmol) and 5 (74.78 mg, 0.25 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. Then dissolved the oil mixture in 2 mL CH2Cl2 and 2 mL TFA was add under argon. The reaction mixture was stirred at room temperature for 12 h (TLC monitor). The solvent was removed under reduce pressure and the crude compound was purified by flash chromatography on silica gel, using HOAc/ethyl acetate (1:100) as the eluent, gave 5a; (100.64 mg, 94.1%). [α]D25: −21.1 (c=0.30, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 8.12 (s, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.71-7.61 (m, 2H), 7.37-7.26 (m, 5H), 6.83 (s, 1H), 5.17-5.15 (m, 1H), 3.45-3.30 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.31, 160.07, 139.09, 137.76, 135.24, 135.13, 129.90, 129.46, 128.84, 127.56, 125.63, 123.89, 122.16, 120.45, 120.40, 119.49, 54.09, 39.26, 29.70; HRMS (ESI): calcd for: C19H13ClF3NO3S [M−H]−=426.0184, obsd [M−H]−=426.0170.

Provenance & Evidence