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

HRID 465387ノート

反応式

HRID 465387 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88565e27c606481f8e1352bcfb61f580
出典データセット
uspto-grants-1992_10
特許番号
US05153203

反応ノート

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