Hydroxyamine hydrochloride → HCID 136338000, compound

HRID 241387Notes

Reaction equation

HRID 241387 reaction equation
[OH:1][C:2]1[C:3]([C:16](=O)[CH2:17][CH2:18][C:19]2[S:20][C:21]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:22]=3[C:23]=2[CH2:24][CH2:25][CH3:26])=[CH:4][C:5]([CH3:15])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl.[NH2:37][OH:38].C([O-])(=O)C.[Na+]>CCO.O>[OH:1][C:2]1[C:3]([C:16](=[N:37][OH:38])[CH2:17][CH2:18][C:19]2[S:20][C:21]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:22]=3[C:23]=2[CH2:24][CH2:25][CH3:26])=[CH:4][C:5]([CH3:15])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 66884659HCID 66884659, compound

Product 1

HCID 136338000HCID 136338000, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of Ethyl 5-hydroxy-2-methyl-4-[3-[3-propyl-6-(trifluoromethyl)benzothiophen-2-yl]propionyl]-phenoxyacetate (obtained in Example 22-(4), 19 mg, 0.0381 mmol) in EtOH (0.4 mL) was added hydroxylamine hydrochloride (2.9 mg, 0.0419 mmol) and sodium acetate (3.8 mg, 0.0457 mmol) in water (0.3 mL). The mixture was heated for 10 hours under reflux and cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from chloroform-hexane, to give the titled compound as a white crystal (7.5 mg, yield 38%).

Workup

  1. temperatureThe mixture was heated for 10 hours
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-80ce2e69336a4308862b6989dbb90e92
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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