Hydrochloric Acid → HCID 59607574, compound

Participants

Reaction Steps

To a solution of 2-methoxythiazole-5-carboxylic acid (80 mg, 0.50 mmol) and (R)-ethyl 3-amino-4-(3′-chlorobiphenyl-4-yl)butanoate hydrochloride (160 mg, 0.45 mmol) in DMF (5 mL) is added HATU (207 mg, 0.55 mmol) and TEA (276 mg, 2.73 mmol). The crude is stirred at room temperature for 2 hrs. The crude is neutralized with 1 N HCl and diluted in water and EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated. The crude is purified via flash chromatography using 30% EtOAc/heptane to 70% EtOAc/heptane to give (R)-ethyl 4-(3′-chlorobiphenyl-4-yl)-3-(2-methoxythiazole-5-carboxamido)butanoate (170 mg). HPLC retention time=1.97 minutes (condition D); MS (m+1)=459.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29 (t, J=7.1 Hz, 3 H) 2.49-2.69 (m, 2 H) 2.93 (dd, J=13.6, 8.1 Hz, 1 H) 3.10 (dd, J=13.5, 6.2 Hz, 1 H) 4.09 (s, 3 H) 4.00-4.15 (m, 2 H) 4.53-4.69 (m, 1 H) 6.78 (d, J=8.6 Hz, 1 H) 7.25-7.32 (m, 3 H) 7.35 (t, J=7.71 Hz, 1 H) 7.44 (dt, J=7.6, 1.5 Hz, 1 H) 7.48-7.54 (m, 3 H) 7.55 (t, J=1.8 Hz, 1 H).

Provenance & Evidence