Hydrochloric Acid → 5-((4-(tert-Butoxycarbonyl)morpholin-2-yl)methoxy)-2'-cyano-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 2-((2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-yloxy)methyl)morpholine-4-carboxylate (107 mg, 0.23 mmol) in THF (2 mL) was added 2.5 M of aq. lithium hydroxide solution (0.52 mL, 1.3 mmol). The reaction mixture was stirred at 60° C. overnight, and then acidified with 15% HCl (aq.) to pH=5, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to get the title compound. 1H NMR (CDCl3, 400 MHz): 7.86 (t, 1H, J=1.6 Hz), 7.70 (t, 1H, J=1.6 Hz), 7.59 (s, 1H), 7.47 (dd, 1H, J=8.0, 1.2 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.37 (s, 1H), 4.20-3.56 (m, 7H), 3.10-2.90 (m, 2H), 2.45 (s, 3H), 1.49 (s, 9H).

Provenance & Evidence