反应 #1340615

反应方程式

hydrochloric acid

sodium hydroxide

ethyl 7-[(3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

→

title compound

收率 58.2%

7-[(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

收率 58.2%

溶剂

ethanol

ethanol

反应条件

后处理

1. 1
   其他was removed under reduced pressure
2. 2
   workup.ADDITIONSubsequently, 1 mol/L hydrochloric acid was added
3. 3
   萃取followed by extraction with ethyl acetate (100 mL×3)
4. 4
   洗涤The ethyl acetate layer was washed by saturated brine (100 mL)
5. 5
   干燥dried over anhydrous sodium sulfate
6. 6
   过滤After filtration
7. 7
   浓缩the filtrate was concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONThe obtained residue was dissolved in concentrated hydrochloric acid (5 mL)
9. 9
   洗涤the solution was washed by chloroform (50 mL)
10. 10
    萃取followed by extraction with chloroform (100 mL×3)
11. 11
    干燥drying over anhydrous sodium sulfate
12. 12
    过滤After filtration
13. 13
    浓缩the filtrate was concentrated under reduced pressure
14. 14
    其他the obtained residue was recrystallized from ethanol

实验过程

A 1 mol/L aqueous sodium hydroxide solution (5 mL, 5 mmol) was added under cooling with ice to ethyl 7-[(3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (957 mg, 1.96 mmol) in ethanol (10 mL), and the mixture was stirred at room temperature for 3 hours. The resultant mixture was neutralized with 1 mol/L hydrochloric acid under cooling with ice, and ethanol was removed under reduced pressure. Subsequently, 1 mol/L hydrochloric acid was added thereto, followed by extraction with ethyl acetate (100 mL×3). The ethyl acetate layer was washed by saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in concentrated hydrochloric acid (5 mL), and the solution was washed by chloroform (50 mL). The pH of the resultant mixture was adjusted to 7.8 with an aqueous sodium hydroxide solution, followed by extraction with chloroform (100 mL×3) and drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was recrystallized from ethanol, to thereby yield the title compound as pale yellow crystals (420 mg, 58.2%).

来源