Hydrochloric Acid → (R)-benzyl 3-amino-4-(3'-chlorobiphenyl-4-yl)butanoate hydrochloride

Participants

Reaction Steps

To (R)-benzyl 3-(tert-butoxycarbonylamino)-4-(3′-chlorobiphenyl-4-yl)butanoate (3.561 g, 7.42 mmol) is added a solution of 4 M HCl in 1,4-dioxane (18.55 mL, 74.2 mmol) at room temperature. After stirring for 4 hours, the reaction mixture is concentrated under reduced pressure to give (R)-benzyl 3-amino-4-(3′-chlorobiphenyl-4-yl)butanoate hydrochloride (3.11 g). HPLC retention time=1.07 minutes (condition B); MS (m+1)=380.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.81 (A of ABX, Jab=17.4 Hz, Jax=4.5 Hz, 1 H) 2.93 (B of ABX, Jab=17.4 Hz, Jbx=7.6 Hz, 1 H) 3.03-3.09 (m, 1 H) 3.50 (dd, J=4.9 and 13.5 Hz, 1 H) 3.98 (br s, 1 H) 5.09 (s, 2 H) 7.24-7.22 (m, 9 H) 7.35-7.38 (m, 1 H) 7.42 (d, J=8.1 Hz, 2 H) 7.48-7.49 (m, 1 H) 8.78 (br s, 3 H).

Provenance & Evidence