Hydrochloric Acid → HCID 44463107, compound

HRID 241386Notes

Reaction equation

HRID 241386 reaction equation
C([OH:3])C.[OH:4][C:5]1[C:6]([C:19](=NO)[CH2:20][CH2:21][C:22]2[S:23][C:24]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:25]=3[C:26]=2[CH2:27][CH2:28][CH3:29])=[CH:7][C:8]([CH3:18])=[C:9]([CH:17]=1)[O:10][CH2:11][C:12]([O:14]CC)=[O:13].O.[OH-].[Li+].Cl>O>[OH:4][C:5]1[C:6]([C:19](=[O:3])[CH2:20][CH2:21][C:22]2[S:23][C:24]3[CH:33]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:31]=[CH:30][C:25]=3[C:26]=2[CH2:27][CH2:28][CH3:29])=[CH:7][C:8]([CH3:18])=[C:9]([CH:17]=1)[O:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 136338000HCID 136338000, compound

Product 1

HCID 44463107HCID 44463107, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethanol (0.2 mL) and water (0.1 mL) was suspended ethyl 5-hydroxy-2-methyl-4-[1-hydroxyimino-3-[3-propyl-6-(trifluoromethyl)-benzothiophen-2-yl]propyl]phenoxyacetate (15 mg, 0.0295 mmol) obtained above. After the addition of lithium hydroxide monohydrate (3.7 mg, 0.0885 mmol), the suspension was heated for 1 hour under reflux, and then allowed to cool to room temperature and diluted with ice-water. The mixture was acidified by addition of 1M HCl and extracted with ethyl acetate. The organic layer was washed with 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 (9.7 mg, yield 69%).

Workup

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

Sources & evidence

ORD record
ord-04c536d7a6cf48878571dda0d8cd4722
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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