Hydrochloric Acid → HCID 136352669, compound

HRID 241388Notes

Reaction equation

HRID 241388 reaction equation
CCO.[OH:4][C:5]1[C:6]([C:19](=[N:38][OH:39])[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](=[N:38][OH:39])[CH2:20][CH2:21][C:22]2[S:23][C:24]3[CH:33]=[C:32]([C:34]([F:36])([F:37])[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]([OH:14])=[O:13]

Participants

6

Reactant 4

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

Product 1

HCID 136352669HCID 136352669, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of EtOH (0.2 mL) and H2O (0.1 mL) was suspended ethyl 5-hydroxy-4-[1-hydroxyimino-3-[3-propyl-6-(trifluoromethyl)-benzothiophen-2-yl]propyl]-2-methylphenoxyacetate (7.5 mg, 0.0143 mmol) obtained above. After the addition of lithium hydroxide monohydrate (1.8 mg, 0.0429 mmol), the mixture was heated for 1 hour under reflux, and then allowed to cool to room temperature and added 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 to give the title compound (8.0 mg, yield>99%) as a brown crystal.

Workup

  1. customobtained above
  2. temperaturethe mixture 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

Sources & evidence

ORD record
ord-8b8076fa6fda4fc8bca29d450461f23f
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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