Water → Ethyl 1-(2,4-difluorophenyl)-7-ethylsulfinyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 246969ノート

反応式

HRID 246969 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:22])=[C:16]([S:19][CH2:20][CH3:21])[N:17]=2)[C:12](=[O:23])[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10]1.ClC1C=CC=C(C(OO)=[O:37])C=1.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:22])=[C:16]([S:19]([CH2:20][CH3:21])=[O:37])[N:17]=2)[C:12](=[O:23])[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10]1

参加物

6

反応物 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13849337Ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

生成物 1

HCID 13849339Ethyl 1-(2,4-difluorophenyl)-7-ethylsulfinyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate収率 77.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 10 ml of methylene chloride was dissolved 1.00 g of ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and 580 mg of m-chloroperbenzoic acid (purity: 80%) was added thereto, after which the resulting mixture was subjected to reaction with ice-cooling for 5 hours. The precipitates were removed by filtration, and to the filtrate thus obtained was added 10 ml of water, after which the pH thereof was adjusted to 7.5 with saturated aqueous sodium hydrogencarbonate solution. The organic layer was thereafter separated, washed with 10 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene-ethyl acetate (10:1 by volume)] to obtain 810 mg (yield 77.9%) of ethyl 1-(2,4-difluorophenyl)-7-ethylsulfinyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 150°-151° C. The physical properties of this compound were identical with those of the compound obtained in Example 44.

後処理

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction with ice-
  3. temperaturecooling for 5 hours
  4. customThe precipitates were removed by filtration
  5. customto the filtrate thus obtained
  6. customThe organic layer was thereafter separated
  7. washwashed with 10 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene-ethyl acetate (10:1 by volume)]

出典と根拠

ORDレコード
ord-41b331f847f848b0a9cba7d868919def
出典データセット
uspto-grants-1987_11
特許番号
US04704459

反応ノート

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