反应 #41266

反应方程式

hydroxylamine hydrochloride

E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid

hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride

→

title compound

收率 45.7%

E-3-[3′-(1-adamantyl)-4′-hydroxy-biphenyl-4-yl]-N-hydroxy-acrylamide

收率 45.7%

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   其他DMF was removed under reduced pressure
3. 3
   洗涤the residue was washed with water
4. 4
   其他to obtain 5 g of a crude product
5. 5
   其他Purification by flash chromatography on silica gel (phosphate buffered)

实验过程

To a solution of E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamic acid (2 g, 5.34 mmol) in 80 ml of DMF were added hydroxybenzotriazole hydrate (866 mg, 5.34 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1130 mg, 6.94 mmol). The mixture was stirred at room temperature for 4 h. After addition of hydroxylamine hydrochloride (1856 mg, 26.7 mmol), followed by 3.7 ml (26.7 mmol) of TEA, the mixture was stirred at room temperature overnight. DMF was removed under reduced pressure and the residue was washed with water to obtain 5 g of a crude product. Purification by flash chromatography on silica gel (phosphate buffered) using as eluent dichloromethane/methanol 95:5 afforded 950 mg of the title compound as a white solid.

来源