Diisopropylethylamine → Ethyl 5-(3-hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylate

Participants

Reaction Steps

To a mixture of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (2.0 g, 7.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.7 g, 14 mmol), 1-hydroxybenzotriazole hydrate (1.1 g, 7.0 mmol), and CH2Cl2 (50 mL) were added 3-hydroxyazetidine hydrochloride (1.2 g, 10 mmol) and N,N-diisopropylethylamine (3.7 mL, 21 mmol). The mixture was stirred at room temperature for 5 h, and then washed with brine and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (0-10% MeOH/CH2Cl2) to afford a syrup. LC-MS: 340.4 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.34 (t, 1H, J=1.6 Hz), 8.19 (t, 1H, J=1.6 Hz), 8.04 (t, 1H, J=1.6 Hz), 7.52 (d, 2H, J=8.4 Hz), 7.28 (d, 2H, J=8.4 Hz), 4.75 (bs, 1H), 4.50 (m, 2H), 4.41 (q, 2H, J=7.2 Hz), 4.25 (bs, 1H), 4.10 (bs, 1H), 2.82 (bs, 1H), 2.41 (s, 3H), 1.42 (t, 3H, J=7.2 Hz).

Provenance & Evidence