Butyric Acid → HCID 57510018, compound

Participants

Reaction Steps

In a 4 mL vial was mixed (Z)—N-(4-(N′-hydroxycarbamimidoyl)phenyl)isoindoline-2-carboxamide (50 mg, 0.169 mmol), butyric acid (0.017 ml, 0.186 mmol), 1-hydroxybenzotriazole hydrate (12.92 mg, 0.084 mmol), and N-methylmorpholine (0.056 ml, 0.506 mmol) in anhydrous dimethylformamide (2 ml). To this solution was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (48.5 mg, 0.253 mmol) and the mixture was stirred overnight at ambient temperature. The solution was diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried with sodium sulfate, decanted, and concentrated. The residue was taken up in anhydrous toluene (1 ml), and the mixture was heated at 110° C. for 2 days. The reaction was diluted with water; and the solids that formed were filtered and washed with water and ether to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.68 (s, 1H), 7.89-7.91 (m, 2H), 7.78-7.80 (m, 2H), 7.36-7.40 (m, 2H), 7.30-7.34 (m, 2H), 4.76-4.85 (m, 4H), 2.96 (t, J=7.4 Hz, 2H), 1.81 (hex, J=7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); MS (ESI(−)) m/e347 (M−H)−.

Provenance & Evidence