تفاعل #1697384

معادلة التفاعل

6-methoxy-1-naphthalenecarboxylic acid

oxalyl chloride

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

sodium hydrogen carbonate

→

title compound

المردود 69.2%

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

المردود 69.2%

المذيبات

tetrahydrofuran

N,N-dimethylformamide

ethyl acetate

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر