Hydroxyamine hydrochloride → 5-(1-Hydroxyimino-2-methylpropyl)thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide

HRID 1351329Notes

Reaction equation

HRID 1351329 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:24])[S:11]([C:14]2[CH:18]=[C:17]([C:19](=O)[CH:20]([CH3:22])[CH3:21])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:24])[S:11]([C:14]2[CH:18]=[C:17]([C:19](=[N:26][OH:27])[CH:20]([CH3:22])[CH3:21])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21098660HCID 21098660, compound

Product 1

HCID 866010025-(1-Hydroxyimino-2-methylpropyl)thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture solution of 5-isobutyrylthiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide (the compound of Preparation Example 88) (30 mg) in ethanol (2 mL) and water (1 mL) was added hydroxylamine.hydrochloride (11 mg) and sodium acetate (13 mg). After heating and refluxing for 12 hours, the reaction solution was cooled to room temperature. The solution was diluted with water and extracted with ethyl acetate. This solution was washed with saturated sodium chloride water. The crude product that was obtained after drying with anhydrous sodium sulfate and removing the solvent by evaporation was purified by silica gel column chromatography (ethyl acetate/hexane), the title compound (a pale yellow viscous oily substance) (29 mg) was obtained as a mixture where (E):(Z)=1:1.

Workup

  1. temperatureAfter heating
  2. temperaturerefluxing for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThis solution was washed with saturated sodium chloride water
  5. customThe crude product that was obtained
  6. dry with materialafter drying with anhydrous sodium sulfate
  7. customremoving the solvent
  8. customby evaporation
  9. customwas purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-283ad932041d4f99b4d4eed331555735
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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