氢化钠 → Ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 465375笔记

反应方程式

HRID 465375 反应方程式
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C1CCN2C(=NCCC2)CC1.[H-].[Na+]>CN(C=O)C>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32]([O:35][C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

参与物

6

反应物 4

HCID 24758氢化钠HCID 81184DBUHCID 535415莫西沙星三氟乙酯HCID 4416939(9H-芴-9-基)甲基 3-羟基吡咯烷-1-羧酸酯

产物 1

HCID 15021538Ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate收率 58.6%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a mixture of 233 mg of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 168 mg of 1-t-butoxycarbonyl-3-hydroxypyrrolidine, 170 mg of DBU and 5 xl of DMF was added 36 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 concentrated to dryness under reduced pressure. After chloroform and 10% citric acid were added to the residue and the resultant mixture was shaken thoroughly, the resulting chloroform layer was collected and then successively washed with a 5% aqueous solution of sodium hydrogencarbonate and saturated saline. The chloroform solution was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel (chloroform/methanol: 100:1), whereby 210 mg of ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate was obtained.

后处理

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. additionAfter chloroform and 10% citric acid were added to the residue
  3. stirringthe resultant mixture was shaken thoroughly
  4. customthe resulting chloroform layer was collected
  5. washsuccessively washed with a 5% aqueous solution of sodium hydrogencarbonate and saturated saline
  6. dry with materialThe chloroform solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (chloroform/methanol: 100:1)

来源与证据

ORD记录
ord-924f6b530c634bd3a526df38747d78fe
来源数据集
uspto-grants-1992_10
专利号
US05153203

反应笔记

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