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

HRID 1253433ノート

反応式

HRID 1253433 の反応式
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]2[CH:26]=[C:25]3[C:20]([C:21](=[O:35])[C:22]([C:30]([O:32]CC)=[O:31])=[CH:23][N:24]3[CH:27]3[CH2:29][CH2:28]3)=[CH:19][C:18]=2[F:36])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C>[C:3]([O:7][C:8]([NH:10][C@H:11]1[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]2[CH:26]=[C:25]3[C:20]([C:21](=[O:35])[C:22]([C:30]([OH:32])=[O:31])=[CH:23][N:24]3[CH:27]3[CH2:29][CH2:28]3)=[CH:19][C:18]=2[F:36])[CH2:12]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67308688Ethyl 7-[(3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

生成物 1

HCID 673087927-[(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%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

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%).

後処理

  1. customwas removed under reduced pressure
  2. additionSubsequently, 1 mol/L hydrochloric acid was added
  3. extractionfollowed by extraction with ethyl acetate (100 mL×3)
  4. washThe ethyl acetate layer was washed by saturated brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in concentrated hydrochloric acid (5 mL)
  9. washthe solution was washed by chloroform (50 mL)
  10. extractionfollowed by extraction with chloroform (100 mL×3)
  11. dry with materialdrying over anhydrous sodium sulfate
  12. filtrationAfter filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customthe obtained residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-3cff4d257ba44f09b487fd7399a1b7b8
出典データセット
uspto-grants-2013_06
特許番号
US08455482B2

反応ノート

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