Реакция #42138
ord-6f6c62e594e144db91daf6c248e0d417
Уравнение реакции
Реактанты
Реагенты
Условия реакции
Обработка
- 1Другоеthe solvent was removed under reduced pressure
- 2workup.DISSOLUTIONThe resulting residue was dissolved in DCM (20 mL)
- 3Промывкаwashed with saturated aqueous sodium bicarbonate solution (10 mL)
- 4СушкаThe organic phase was then dried over MgSO4
- 5Другоеthe solvent was removed under reduced pressure
- 6ДругоеThe crude product was purified by flash chromatography (5-10% MeOH/DCM)
- 7Другоеto give a solid, which
- 8workup.STIRRINGstirred at room temperature for 2 hours
- 9ДругоеThe solvent was then removed under reduced pressure
- 10workup.DISSOLUTIONthe crude residue was dissolved in DCM (30 mL)
- 11Промывкаwashed with 1N NaOH (15 mL)
- 12ДругоеThe organic phase was separated
- 13Сушкаdried over MgSO4
- 14Фильтрацияfiltered
- 15Другоеthe solvent was removed under reduced pressure
Методика
To a stirred solution of 4-(N-tert-butoxycarbonylaminomethyl)aniline (756 mg, 3.4 mmol), 3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic acid (1.5 g, 4.08 mmol; prepared as described in Preparation 11) and HATU (1.55 g, 4.08 mmol) in DMF (6.8 mL), was added DIPEA (770 mL, 4.42 mmol). The reaction mixture was stirred at 50° C. overnight, and then the solvent was removed under reduced pressure. The resulting residue was dissolved in DCM (20 mL) and washed with saturated aqueous sodium bicarbonate solution (10 mL). The organic phase was then dried over MgSO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (5-10% MeOH/DCM) to give a solid, which was dissolved in TFA/DCM (25%, 30 mL) and stirred at room temperature for 2 hours. The solvent was then removed under reduced pressure and the crude residue was dissolved in DCM (30 mL) and washed with 1N NaOH (15 mL). The organic phase was separated, dried over MgSO4, filtered and the solvent was removed under reduced pressure to give 1.5 g of the title intermediate (94% yield over 2 steps).