Sodium Hydroxide → 8-Chloro-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-ene-3-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2256089ノート

反応式

HRID 2256089 の反応式
[Cl:1][C:2]1[C:3](F)=[C:4]([F:20])[CH:5]=[C:6]2[C:11]=1[N:10]([C@@H:12]1[CH2:14][C@@H:13]1[F:15])[CH:9]=[C:8]([C:16]([OH:18])=[O:17])[C:7]2=[O:19].Br.Br.[C:24]12[CH2:31][NH:30][CH2:29][C:28]=1[CH2:27][NH:26][CH2:25]2.C1CCN2C(=NCCC2)CC1.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[C:3]([N:26]2[CH2:27][C:28]3[CH2:29][NH:30][CH2:31][C:24]=3[CH2:25]2)=[C:4]([F:20])[CH:5]=[C:6]2[C:11]=1[N:10]([C@@H:12]1[CH2:14][C@@H:13]1[F:15])[CH:9]=[C:8]([C:16]([OH:18])=[O:17])[C:7]2=[O:19]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104485478-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

生成物 1

HCID 543611928-Chloro-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-ene-3-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 10.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 318 mg of 8-chloro-6,7-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 544 mg of 3,7-diazabicyclo[3.3.0]oct-1(5) -ene dihydrobromide (JP-A-3-193779) and 2 ml of DBU in 20 ml of acetonitrile was heated under reflux for 15 hours. To the mixture was added 1N sodium hydroxide, and an insoluble material was removed by filtration. To the filtrate, was added hydrochloric acid till pH became 7.4, and the mixture was extracted by five 50 ml portions of chloroform. A combined organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was recrystallized from a mixture of ethanol and ammonia water to yield 43.7 mg of the titled compound.

後処理

  1. temperatureunder reflux for 15 hours
  2. customan insoluble material was removed by filtration
  3. additionTo the filtrate, was added hydrochloric acid
  4. extractionthe mixture was extracted by five 50 ml portions of chloroform
  5. dry with materialA combined organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was recrystallized from a mixture of ethanol and ammonia water

出典と根拠

ORDレコード
ord-182e778db8e14171b6fddad6184f080b
出典データセット
uspto-grants-1997_08
特許番号
US05654318

反応ノート

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