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(Diethylamino)sulfur trifluoride → Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1584818
ノート
印刷プレビュー

反応式

HRID 1584818 の反応式
[Br:1][C:2]1[C:11]([CH2:12]O)=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23].C(N(S(F)(F)[F:30])CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:11]([CH2:12][F:30])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 21220404Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

生成物 1

HCID 21220400Ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

In 127 ml of methylene chloride was suspended 1.27 g of ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, and 1.33 g of diethylaminosulfur trifluoride was dropwise added to the suspension at -40° C., after which the resulting mixture was stirred at -20° C. for one hour and then at 0° C. for three hours. The reaction mixture was added to 120 ml of ice water and the pH was adjusted to 8 with a saturated aqueous sodium hydrogencarbonate solution. Thereafter, the organic layer formed was separated, washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluent: chloroform:ethanol=100:1), to obtain 1.05 g of colorless, crystalline ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate.

後処理

  1. additionwas dropwise added to the suspension at -40° C.
  2. waitat 0° C. for three hours
  3. customThereafter, the organic layer formed
  4. customwas separated
  5. washwashed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluent: chloroform:ethanol=100:1)

出典と根拠

ORDレコード
ord-5718d3e101064c7595b275e68965cc43
出典データセット
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05935952

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート