反応 #88183
ord-3980f80b95d54813af43c984dd55e2ae
反応方程式
反応物
試薬
反応条件
後処理
- 1温度maintaining the temperature at 15° C
- 2温度The reaction mixture was warmed to 20-25° C.
- 3濃縮The reaction mixture was concentrated under reduced pressure
- 4その他the residue was partitioned between water (200 mL) and pentane-ethyl acetate (1:2, 300 mL)
- 5抽出The aqueous phase was further extracted with ethyl acetate (2 times with 100 mL)
- 6洗浄The combined organic extracts were rinsed sequentially with water (200 mL), saturated aqueous sodium bicarbonate solution (2 times with 100 mL), and brine (2 times with 25 mL)
- 7乾燥The organic layer was then dried over sodium sulfate
- 8ろ過filtered
- 9濃縮concentrated
実験手順
To a 500-mL 3-neck flask was added methyl 3-(aminomethyl)benzoate hydrochloride (12.9 g, 64.1 mmol) followed by DMSO (26 mL). The solution was cooled to 15° C. N-Methyl morpholine (27 mL, 240 mmol) was added followed by EDCl (13 g, 68 mmol) and HOBT (4.09 g, 30 mmol), maintaining the temperature at 15° C. A solution of (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (20.94 g, 60.98 mmol) in THF (100 mL) was added dropwise over 10 min. The reaction mixture was warmed to 20-25° C. and stirred for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between water (200 mL) and pentane-ethyl acetate (1:2, 300 mL). The aqueous phase was further extracted with ethyl acetate (2 times with 100 mL). The combined organic extracts were rinsed sequentially with water (200 mL), saturated aqueous sodium bicarbonate solution (2 times with 100 mL), and brine (2 times with 25 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated to afford (R)-methyl 3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)benzoate (22.3 g). MS (ES+) 491.3 (M+H).