Reacción #1697406

Ecuación de reacción

4-n-butylbenzoic acid

oxalyl chloride

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

sodium hydrogen carbonate

→

title compound

Rendimiento 64.0%

4-butyl-N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)benzamide

Rendimiento 64.0%

Disolventes

tetrahydrofuran

N,N-dimethylformamide

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction solution was evaporated under reduced pressure
2. 2
   workup.STIRRINGthe mixture was stirred overnight at room temperature
3. 3
   Extracciónextracted with ethyl acetate (50 ml×2)
4. 4
   LavadoThe extract was washed with saturated brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Otroevaporated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1)
8. 8
   OtroRecrystallization from ethyl acetate-hexane

Procedimiento

To a solution of 4-n-butylbenzoic acid (153 mg, 0.86 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.15 ml, 1.72 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 (200 mg, 0.57 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=4:1-1:1). Recrystallization from ethyl acetate-hexane gave the title compound (172 mg, 64%).

Fuente