反应 #1702172

反应方程式

trifluoroacetic acid

5,5,5-trifluoropentanoic acid

EDC

triethylamine

isoxazole

→

3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

溶剂

methylene chloride

methylene chloride

water

反应条件

后处理

1. 1
   workup.ADDITIONare added
2. 2
   洗涤The organic layer was washed with saturate sodium bicarbonate (2×)
3. 3
   干燥dried over magnesium sulfate
4. 4
   浓缩concentrated
5. 5
   其他to provide a white solid which
6. 6
   其他was purified by flash silica gel chromatography (gradient of ethyl acetate/methanol)

实验过程

3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole III-57 was synthesized in two steps from compound III-53 starting with deprotection using analogous conditions to Example 11. The resulting trifluoroacetic acid salt (1.0 equiv) is then dissolved in methylene chloride (0.11 M with respect to isoxazole after which 5,5,5-trifluoropentanoic acid (1.5 equiv), EDC (1.5 equiv) and triethylamine (3.0 equiv) are added. The reaction is allowed to stir for 14 h at room temperature after which point the reaction was transferred to a separatory funnel with excess water and methylene chloride. The organic layer was washed with saturate sodium bicarbonate (2×), dried over magnesium sulfate, and concentrated to provide a white solid which was purified by flash silica gel chromatography (gradient of ethyl acetate/methanol). [M+H]+=373.7 m/z. Activity: C

来源