Hydroxyamine hydrochloride → HCID 21098697, compound

HRID 1351328Notes

Reaction equation

HRID 1351328 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:28])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:26])[CH3:25])[C:19](=O)[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31]>N1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:28])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:26])[CH3:25])/[C:19](=[N:30]/[OH:31])/[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21098664HCID 21098664, compound

Product 1

HCID 21098697HCID 21098697, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-acetoxy-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide (the compound of Preparation Example 65) (200 mg) in pyridine (2 mL) was added hydroxylamine.hydrochloride (61 mg). After stirring at room temperature for 2.5 hours, two products were observed by TLC. After the solution was diluted with ethyl acetate, the solution was washed with water and saturated sodium chloride water. The crude products obtained after drying with anhydrous sodium sulfate, removing the solvent by evaporation were purified by silica gel column chromatography (ethyl acetate/hexane), the fraction that was eluted by a solvent with a higher polarity (the fractions that demonstrated low Rf values) were collected, and (7Z)-6-acetoxy-7-hydroxyimino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amide was obtained. Thereafter, to methanol (1 mL) was added excess potassium carbonate. The solution was stirred at room temperature for 1 hour. Water was added, the solution was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. The residue resulting from the removal of the solvent by evaporation was purified by LC-MS, and the title compound (0.9 mg) was obtained as a colorless solid.

Workup

  1. washthe solution was washed with water and saturated sodium chloride water
  2. customThe crude products obtained
  3. dry with materialafter drying with anhydrous sodium sulfate
  4. customremoving the solvent
  5. customby evaporation
  6. customwere purified by silica gel column chromatography (ethyl acetate/hexane)
  7. washthe fraction that was eluted by a solvent with a higher polarity (the fractions that
  8. customwere collected

Sources & evidence

ORD record
ord-3a3ea6f7a893465b85f8f22c9f1dd933
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…