Sodium Hydroxide → 7-(1-t-Butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 465387노트

반응식

HRID 465387 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]([F:24])=[C:22]3[C:17]([C:18](=[O:33])[C:19]([C:28]([O:30]CC)=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[CH:16][C:15]=2[F:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]([F:24])=[C:22]3[C:17]([C:18](=[O:33])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[CH:16][C:15]=2[F:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 15021538Ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

생성물 1

HCID 150215827-(1-t-Butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid수율 92.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 1.28 g of ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 3.5 ml of 1N aq. sodium hydroxide solution and 30 ml of tetrahydrofuran was heated under reflux for 1.5 hours. The mixture was concentrated under reduced pressure. To the residue was added 10% aq. citric acid to acidify the same, followed by extraction with chloroform. The chloroform layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then concentrated to dryness. The residue was recrystallized from chloroform-diisopropyl ether, whereby 1.11 g of the title compound was obtained as colorless powder.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionTo the residue was added 10% aq. citric acid
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform layer was washed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe residue was recrystallized from chloroform-diisopropyl ether

출처 및 근거

ORD 기록
ord-88565e27c606481f8e1352bcfb61f580
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153203

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