Реакция #42339
ord-850f8369adcb4fd8b5fa402985e7cbc3
Уравнение реакции
Реактанты
Реагенты
Условия реакции
Обработка
- 1workup.ADDITIONis added
- 2Промывкаwashed with 1 N hydrochloric acid (25 mL), saturated sodium bicarbonate (25 mL), and brine
- 3Сушкаdried (magnesium sulfate)
- 4Фильтрацияfiltered
- 5Концентрированиеconcentrated under reduced pressure
- 6ДругоеPurification by flash column chromatography (silica, 1:9 methanol/chloroform)
Методика
A solution of 3-[(dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid (209 mg, 0.63 mmol), HATU (359 mg, 0.95 mmol), HOBt (128 mg, 0.95 mmol), and diisopropylethylamine (165 μL, 0.95 mmol) is stirred in methylene chloride (2.0 mL) for 15 min. A solution of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride prepared by the method in Example SP-272 (257 mg, 0.63 mmol) and diisopropylethylamine (165 μL, 0.95 mmol) in methylene chloride (2.0 mL) is added and the reaction mixture is stirred overnight. The reaction mixture is diluted with methylene chloride, washed with 1 N hydrochloric acid (25 mL), saturated sodium bicarbonate (25 mL), and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 methanol/chloroform) provides the title compound as the free base. The solid is dissolved in methanol (1 mL), and treated with hydrochloric acid (0.3 mL of a 1.0 M solution in diethyl ether, 0.3 mmol). The resulting precipitate is collected by filtration to provide the title compound. APCI MS m/z 648.4 [M+H]+.