تفاعل #1340615

معادلة التفاعل

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

المردود 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

المردود 58.2%

المذيبات

ethanol

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىwas removed under reduced pressure
2. 2
   workup.ADDITIONSubsequently, 1 mol/L hydrochloric acid was added
3. 3
   استخلاصfollowed by extraction with ethyl acetate (100 mL×3)
4. 4
   غسيلThe ethyl acetate layer was washed by saturated brine (100 mL)
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   ترشيحAfter filtration
7. 7
   تركيزthe filtrate was concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONThe obtained residue was dissolved in concentrated hydrochloric acid (5 mL)
9. 9
   غسيلthe solution was washed by chloroform (50 mL)
10. 10
    استخلاصfollowed by extraction with chloroform (100 mL×3)
11. 11
    تجفيفdrying over anhydrous sodium sulfate
12. 12
    ترشيحAfter filtration
13. 13
    تركيزthe filtrate was concentrated under reduced pressure
14. 14
    أخرىthe obtained residue was recrystallized from ethanol

الإجراء التجريبي

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%).

المصدر