| 93.4% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h; |
(R)-Quinuclidin-3-yl 6-((R)-2-aminomethyl-morpholin) hexanoate 9b (1.67 g, 4.93 mmol) was dissolved in 100 mL of dichloromethane with stirring, and added with <strong>[108282-38-8]4-amino-5-chloro-2-ethoxy-benzoic acid</strong> (1.17 g, 5.42 mmol) and 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (1.89 g, 9.86 mmol). The reaction mixture was stirred for 3 hours at room temperature and monitored by thin layer chromatography until the disappearance of the starting materials. The mixture was quenched with 100 mL of saturated sodium bicarbonate solution, and extracted with dichloromethane (400 mL×3). The combined organic phase was washed successively with water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from n-hexane/ethyl acetate to obtain the title compound (R)-quinuclidin-3-yl 6-((R)-2-((4-amino-5-chloro-2-ethoxybenzamido)methyl) morpholino)hexanoate 9 (2.47 g, yield 93.4%) as a white solid.MS m/z (ESI): 537.3 [M+1].1H NMR (CDCl3, 400 MHz) delta 8.2 (s, 1H), 8.1 (s, 1H), 6.27 (s, 1H), 4.8 (m, 1H), 4.40 (s, 2H), 4.1-4.05 (q, 2H, J=6.8 Hz), 3.88 (d, 1H, J=6.4 Hz), 3.71-3.66 (m, 3H), 3.37-3.31 (m, 1H), 3.28-3.22 (m, 1H), 2.92-2.68 (m, 7H), 2.34-2.3 (m, 4H), 2.15-2.08 (m, 1H), 2.02-2.01 (m, 1H), 1.93-1.86 (m, 2H), 1.74-1.69 (m, 3H), 1.49-1.47 (m, 3H), 1.49-1.47 (t, 3H, J=6.8 Hz), 1.4-1.3 (m, 3H). |
|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h; |
(R)-Quinuclidin-3-yl 6-((R)-2-aminomethyl-morpholin) hexanoate 9b (1.67 g, 4.93 mmol) was dissolved in 100 mL of dichloromethane with stirring, and added with <strong>[108282-38-8]4-amino-5-chloro-2-ethoxy-benzoic acid</strong> (1.17 g, 5.42 mmol) and 1-ethyl-3-(3-dimethyl-propyl)carbodiimide hydrochloride(1.89 g, 9.86 mmol). The reaction mixture was stirred for 3 hours at room temperature and monitored by thin layer chromatography until the disappearance of the starting materials. The mixture was quenched with 100 mL of saturated sodium bicarbonate solution, and extracted with dichloromethane (400 mL×3). The combined organic phase was washed successively with water (300 mL) and saturated brine (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from n-hexane/ethyl acetate to obtain the title compound (R)-quinuclidin-3-yl 5-((R)-2-((4-amino-5-chloro-2-ethoxybenzamido)methyl)morpholino)hexanoate 9 (2.47 g, yield 93.4%) as a white solid. MS m/z (ESI): 537.3 [M+1]. 1H NMR (CDCl3, 400 MHz) delta 8.2 (s, 1H), 8.1 (s, 1H), 6.27 (s, 1H), 4.8 (m, 1H), 4.40 (s, 2H), 4.1-4.05 (q, 2H, J=6.8Hz), 3.88 (d, 1H, J=6.4Hz), 3.71-3.66 (m, 3H), 3.37-3.31 (m, 1H), 3.28-3.22 (m, 1H), 2.92-2.68 (m, 7H), 2.34-2.3 (m, 4H), 2.15-2.08 (m, 1H), 2.02-2.01 (m, 1H), 1.93-1.86 (m, 2H), 1.74-1.69 (m, 3H), 1.49-1.47 (m, 3H), 1.49-1.47 (t, 3H, J=6.8Hz), 1.4-1.3 (m, 3H). |
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