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

HRID 1351327Notes

Reaction equation

HRID 1351327 reaction equation
[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

Participants

6

Reactant 4

HCID 962Water2×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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-60bb0ebaf67f4ebab38e70d57db924b3
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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