반응 #155332

반응 방정식

hydrochloric acid ethyl acetate

tert-butyl 4-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetylamino}piperidine-1-carboxylate

→

2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-piperidin-4-ylacetamide

수율 27.5%

용매

ethanol

반응 조건

후처리

1. 1
   농축The resulting mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONAfter adding an aqueous sodium bicarbonate solution to the residue
3. 3
   세척the residue was washed with ethyl acetate
4. 4
   workup.ADDITIONA 2N aqueous sodium hydroxide solution was added to the water layer
5. 5
   추출followed by extraction
6. 6
   세척The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was recrystallized from ethanol-ethyl acetate

실험 절차

A 4N hydrochloric acid ethyl acetate solution (25 ml) was added to an ethanol solution (12 ml) of tert-butyl 4-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetylamino}piperidine-1-carboxylate (820 mg, 1.44 mmol), followed by stirring at room temperature for 28 hours. The resulting mixture was concentrated under reduced pressure. After adding an aqueous sodium bicarbonate solution to the residue to adjust the pH to 8, the residue was washed with ethyl acetate. A 2N aqueous sodium hydroxide solution was added to the water layer to adjust its pH to 11, followed by extraction using dichloromethane. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from ethanol-ethyl acetate, giving a white powder of 2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-piperidin-4-ylacetamide (185 mg, yield: 27%).

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