Reacción #1340615

Ecuación de reacción

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

Rendimiento 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

Rendimiento 58.2%

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed under reduced pressure
2. 2
   workup.ADDITIONSubsequently, 1 mol/L hydrochloric acid was added
3. 3
   Extracciónfollowed by extraction with ethyl acetate (100 mL×3)
4. 4
   LavadoThe ethyl acetate layer was washed by saturated brine (100 mL)
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   FiltraciónAfter filtration
7. 7
   Concentraciónthe filtrate was concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONThe obtained residue was dissolved in concentrated hydrochloric acid (5 mL)
9. 9
   Lavadothe solution was washed by chloroform (50 mL)
10. 10
    Extracciónfollowed by extraction with chloroform (100 mL×3)
11. 11
    Secadodrying over anhydrous sodium sulfate
12. 12
    FiltraciónAfter filtration
13. 13
    Concentraciónthe filtrate was concentrated under reduced pressure
14. 14
    Otrothe obtained residue was recrystallized from ethanol

Procedimiento

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%).

Fuente