Sodium Hydroxide → 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid

HRID 561154노트

반응식

HRID 561154 반응식
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27]CC)=[O:26])=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1.[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:7]2[CH:16]1[CH2:17][CH2:18]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 59002984Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate

생성물 1

HCID 590030445-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid수율 62,953,556%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylate (980 mg, 2.36 nmol) and 1M aq. NaOH (5 mL) in EtOH (15 mL) was stirred at 50° C. for 24 h. After the reaction mixture was concentrated in vacuo, the residue was dissolved in water and 2M HCl was added to pH<3. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1) to yield 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid (574 mg, 63%) as a yellow amorphous solid.

후처리

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. addition2M HCl was added to pH<3
  4. extractionThe crude product was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe crude product was purified by column chromatography (Hexane:EtOAc 5:1→1:1)

출처 및 근거

ORD 기록
ord-da13fc96bdc147d3b447094618053b06
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063221B2

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