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Sodium hydride → 7-(t-Butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-5-amino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 465376
ノート
印刷プレビュー

反応式

HRID 465376 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[C:24]([O:28][C:29]([N:31]1[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1.[H-].[Na+]>C(Cl)(Cl)Cl.CS(C)=O>[C:24]([O:28][C:29]([N:31]1[CH2:35][CH2:34][CH:33]([O:36][C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([NH2:17])[C:10]=2[F:16])[CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 44169391-Boc-3-pyrrolidinolHCID 14127986Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

生成物 1

HCID 150215497-(t-Butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-5-amino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 30.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6212Chloroform溶媒

実験手順

To a mixture of 277 mg of ethyl 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 318 mg of 1-t-butoxycarbonyl-3-hydroxypyrrolidine, 194 mg of DBU and 3 ml of DMSO was added 74 mg of 55% sodium hydride while the former was stirred at room temperature. After the resultant mixture was stirred for 1 hour at room temperature, the reaction mixture was diluted with chloroform and then successively washed with 10% citric acid and saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to dryness. The residue was recrystallized from ethanol, whereby 120 mg of 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-5-amino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid was obtained.

後処理

  1. washsuccessively washed with 10% citric acid and saturated saline
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-4879574beb60430a9f39e4a83b573810
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05153203

反応ノート

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