Methanol → 5-(3-Hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acid

Participants

Reaction Steps

A mixture of ethyl 5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylate (2.0 g, 5.9 mmol), lithium hydroxide (0.56 g, 24 mmol), methanol (100 mL), and water (10 mL) was stirred at rt for 4 h. LC-MS indicated completion of the reaction. The solvent was removed in vacuo and the residue was treated with water and acidified with 1N aq. HCl to pH 2-3 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to yield a white solid. LC-MS: 312.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 13.30 (bs, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.03 (s, 1H), 7.64 (d, 2H, J=8.0 Hz), 7.32 (d, 2H, J=8.0 Hz), 5.79 (bs, 1H), 4.52 (s, 2H), 4.30 (bs, 1H), 4.10 (bs, 1H), 3.84 (d, 1H, J=9.6 Hz), 2.37 (s, 3H).

Provenance & Evidence