تفاعل #88183
ord-3980f80b95d54813af43c984dd55e2ae
معادلة التفاعل
المتفاعلات
الكواشف
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المعالجة
- 1درجة الحرارةmaintaining the temperature at 15° C
- 2درجة الحرارةThe reaction mixture was warmed to 20-25° C.
- 3تركيزThe reaction mixture was concentrated under reduced pressure
- 4أخرىthe residue was partitioned between water (200 mL) and pentane-ethyl acetate (1:2, 300 mL)
- 5استخلاصThe aqueous phase was further extracted with ethyl acetate (2 times with 100 mL)
- 6غسيلThe 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)
- 7تجفيفThe organic layer was then dried over sodium sulfate
- 8ترشيحfiltered
- 9تركيزconcentrated
الإجراء التجريبي
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).