反应详情

A mixture of 3-(2-aminoethyl)indole hydrochloride (0.46 g), triethylamine (0.6 ml) and N,N-dimethylformamide (20 ml) was stirred at room temperature for 1 hr. To the obtained mixture was added 3-(5-phenyl-4-isoxazolyl)propionic acid (0.42 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.37 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.45 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and N-[2-(3-indolyl)ethyl]-3-(5-phenyl-4-isoxazolyl)propionamide (0.63 g, yield 91%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR (CDCl3) δ: 2.32–2.44 (2H, m), 2.88–3.04 (4H, m), 3.54–3.66 (2H, m), 5.45 (1H, br s), 6.93 (1H, d, J=2.2 Hz), 7.04–7.28 (2H, m), 7.32–7.62 (5H, m), 7.64–7.74 (2H, m), 8.05 (1H, br s), 8.17 (1H, s).

1. stirringthe mixture was stirred at room temperature overnight
2. extractionthe mixture was extracted with ethyl acetate
3. washThe ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate
4. dry with materialsaturated brine, dried (MgSO4)
5. concentrationconcentrated