Hydrochloric Acid → (R)-ethyl 3-amino-4-(5'-fluoro-2'-methoxybiphenyl-4-yl)butanoate hydrochloride

Participants

Reaction Steps

A solution of (R)-ethyl 3-(tert-butoxycarbonylamino)-4-(5′-fluoro-2′-methoxybiphenyl-4-yl)butanoate, (2.86 g, 6.62 mmol) in 4M HCl in 1,4-dioxane (33.1 ml, 132 mmol) is stirred at room temperature. After stirring for 1 hour, the reaction mixture is concentrated under reduced pressure to give (R)-ethyl 3-amino-4-(5′-fluoro-2′-methoxybiphenyl-4-yl)butanoate hydrochloride salt (2.44 g). HPLC retention time=1.46 minutes (condition A); MS (m+1)=332.3; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (t, J=6.4 Hz, 3 H) 2.66-2.77 (m, 1 H) 2.78-2.91 (m, 1 H) 2.94-3.10 (m, 1 H) 3.42-3.53 (m, 1 H) 3.67 (s, 3 H) 3.83-3.96 (m, 1 H) 4.07 (q, J=6.8 Hz, 2 H) 6.77-6.84 (m, 1 H) 6.87-6.96 (m, 2 H) 7.23 (d, J=7.1 Hz, 2 H) 7.38 (d, J=7.1 Hz, 2 H) 8.64 (br. s., 2 H)

Provenance & Evidence