反应 #1697384

反应方程式

6-methoxy-1-naphthalenecarboxylic acid

oxalyl chloride

(1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride

sodium hydrogen carbonate

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title compound

收率 69.2%

N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-6-(methyloxy)-1-naphthalenecarboxamide

收率 69.2%

溶剂

tetrahydrofuran

N,N-dimethylformamide

ethyl acetate

water

反应条件

后处理

1. 1
   其他The reaction solution was evaporated under reduced pressure
2. 2
   workup.STIRRINGthe mixture was stirred overnight at room temperature
3. 3
   萃取extracted with ethyl acetate (50 ml×2)
4. 4
   洗涤The extract was washed with saturated brine
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   其他evaporated under reduced pressure
7. 7
   其他The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
8. 8
   其他recrystallized from ethyl acetate-hexane

实验过程

To a solution of 6-methoxy-1-naphthalenecarboxylic acid (129 mg, 0.64 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.28 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml) were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (150 mg, 0.43 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml), and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) and recrystallized from ethyl acetate-hexane to give the title compound (148 mg, 69%).

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