Hydroxyamine hydrochloride → Methyl 3-[4-[1-hydroxyimino-3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propyl]-2-methylphenyl]-propionate

HRID 241376Notes

Reaction equation

HRID 241376 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:23]([CH3:33])[CH:22]=1)=O)([CH3:3])[CH3:2].Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+]>CCO.O>[OH:36][N:35]=[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:23]([CH3:33])[CH:22]=1)[CH2:18][CH2:17][C:5]1[S:6][C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 66883002Methyl 3-[4-[3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propionyl]-2-methylphenyl]propionate

Product 1

HCID 86652868Methyl 3-[4-[1-hydroxyimino-3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propyl]-2-methylphenyl]-propionateYield 74.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 3-[4-[3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propionyl]-2-methylphenyl]propionate [Example 12 (7)] (70 mg, 0.15 mmol) in EtOH (1.5 ml) was added a solution of hydroxylamine hydrochloride (11 mg, 0.15 mmol) and sodium acetate (14.5 mg, 0.176 mmol) in water (1 mL). The mixture was heated under reflux for 1 hour, cooled at room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a pale yellow crystal (55 mg, 57%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-13d89d2e8ebf4bfabcc4ca730725a7e6
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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