Triethylamine → HCID 69000154, compound

Participants

Reaction Steps

To a mixture of 2-amino-3-hydroxybenzoic acid hydrobromide (0.50 g, 2.13 mmol) and cyclobutanecarbonyl chloride (0.24 mL, 2.13 mmol) in dichloromethane (20 mL) was added triethylamine (0.90 mL, 6.41 mmol) dropwise, then the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with dichloromethane, and then washed with 2 N HCl. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in toluene (8 mL) and the solution was treated with p-toluenesulfonic acid monohydrate (676 mg, 3.56 mmol). The reaction mixture was then heated to reflux for 5 h. The reaction was cooled to room temperature, poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by re-crystallization from ethyl acetate and hexanes to afford 2-cyclobutylbenzoxazole-4-carboxylic acid (420 mg, 73%) as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ 12.96 (br s, 1H), 7.92 (dd, J=8.1, 0.8 Hz, 1H), 7.84 (dd, J=7.6, 0.8 Hz, 1H), 7.44 (t, J=7.9 Hz, 1H), 3.95-3.85 (m, 1H), 2.46-2.39 (m, 4H), 2.28-2.00 (m, 2H); MS (ESI+) m/z 218 (M+H).

Provenance & Evidence