Benzoyl chloride → HCID 49793048, compound

Participants

Reaction Steps

At 0° C., 0.65 mmol of benzoyl chloride was slowly added to (3R)-3-(3-amino-4-chlorophenyl)-4-(2,2,2-trifluoroacetylamino)butanoate (200 mg, 0.59 mmol) (65b), the diisopropylethylamine (1.13 mL, 0.65 mmol) of (3R)-3-(3-amino-4-chlorophenyl)-4-(2,2,2-trifluoroacetylamino)butanoate, and 113 mL (0.65 mmol) of diisopropylethyl amine in 15 mL of dichloromethane. The reaction solution was stirred for 3 h at room temperature. The reaction mixture was then washed with 1N HCl and saturated sodium bicarbonate solution. The solvent was removed under reduced pressure. The residue, methyl (3R)-3-[3-(acetylamino)-4-chlorophenyl]-4-(2,2,2-trifluoroacetylamino)butanoate, was dissolved in 2.5 mL of methanol and 0.2 mL 2N sodium hydroxide. The solution was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was purified by preparative HPLC to provide the title compound (65). 1H NMR (400 MHz, CD3OD): δ7.97 (d, J=8.0 Hz, 2H), 7.69 (s, 1H), 7.63-7.59 (m, 1H), 7.55-7.50 (m, 2H), 7.27 (d, J=8.0 Hz, 1H), 3.47-3.18 (m, 3H), 2.81 (dd, J=16.0, 8.0 Hz, 1H), 2.70 (dd, J=16.0, 8.0 Hz, 1H); MS (ESI) m/z 333.1 (M+H)+.

Provenance & Evidence