反応 #1340615

反応方程式

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

収率 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

収率 58.2%

溶媒

ethanol

ethanol

反応条件

後処理

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

実験手順

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%).

出典