Triethylamine → HCID 19069319, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of cyclobutanecarboxylic acid (0.26 g, 2.6 mmol), 4-phenoxybenzylamine hydrochloride (0.62 g, 2.6 mmol), HOBt, (0.71 g, 5.2 mmol) and triethylamine (1.1 mL, 7.83 mmol) in THF (9 mL) was added EDCl (0.55 g, 2.6 mmol). The mixture was stirred for 18 hours at room temperature. The solvent was removed, and the residue was suspended in ether and washed with 0.1N HCl, 5% NaHCO3 and brine. The ether layer was dried (MgSO4), filtered through a plug of silica gel and concentrated in vacuo to provide 0.70 g (96%) of the title compound as a white solid. m.p. 69°-71° C. 1H NMR (CDCl3, 300 MHz) δ1.80-2.06 (m, 2H), 2.10-2.14 (m, 2H), 2.15-2.39 (m, 2H), 3.02 (pd, J=7.5, 1.2 Hz, 1H), 4.41 (d, J=6 Hz, 2H), 5.55 (br s, 1H), 6.94-7.04 (m, 4H), 7.08-7.15 (tt, J=7.5, 1.5 Hz, 1H), 7.20-7.28 (m, 2H), 7.30-7.38 (m, 2H). MS (DCl/NH3) m/e 282 (M+H)+.

Provenance & Evidence