Water → (7Z)-N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]-7-hydroxyimino-N-methyl-5,6-dihydro-4H-1-benzothiophene-3-sulfonamide

HRID 1351327ノート

反応式

HRID 1351327 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:25])[CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:18]3[CH2:19][CH2:20][CH2:21][C:22](=O)[C:17]=3[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[OH2:26].Cl.[NH2:28]O.C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:25])[CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:18]3[CH2:19][CH2:20][CH2:21]/[C:22](=[N:28]/[OH:26])/[C:17]=3[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 69415007N-[(2S)-2-(4-Fluorophenyl)-2-hydroxyethyl]-N-methyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-sulfonamide

生成物 1

HCID 11486354(7Z)-N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]-7-hydroxyimino-N-methyl-5,6-dihydro-4H-1-benzothiophene-3-sulfonamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of N-[(2S)-2-(4-fluorophenyl)-2-hydroxyethyl]-N-methyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-sulfonamide (the compound of Preparation Example 49) (370 mg) in ethanol (4 mL) and water (2 mL) was added hydroxylamine.hydrochloride (100 mg) and sodium acetate (118 mg). After heating at 50° C. for 4 hours, the reaction solution was cooled to room temperature, the solution was dilued with water and extracted with ethyl acetate, and then was washed with saturated sodium chloride water. The crude product that was obtained after drying the solution with anhydrous sodium sulfate and removing the solvent by evaporation was purified by silica gel column chromatography (ethyl acetate/hexane; ethyl acetate 10–40%), fraction that was eluted with a solvent of higher polarity (the fractions that demonstrated low Rf values) was collected, and the title compound (280 mg) was obtained as a colorless solid. The NMR data of the present compound were consistent with those described in Example 1

後処理

  1. temperaturethe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwas washed with saturated sodium chloride water
  4. customThe crude product that was obtained
  5. dry with materialafter drying the solution with anhydrous sodium sulfate
  6. customremoving the solvent
  7. customby evaporation
  8. customwas purified by silica gel column chromatography (ethyl acetate/hexane; ethyl acetate 10–40%), fraction that
  9. washwas eluted with a solvent of higher polarity (the fractions that
  10. customwas collected

出典と根拠

ORDレコード
ord-60bb0ebaf67f4ebab38e70d57db924b3
出典データセット
uspto-grants-2007_05
特許番号
US07217723B2

反応ノート

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