Hydrochloric Acid → (1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid

HRID 238961Notes

Reaction equation

HRID 238961 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH:14]=[O:15])=[CH:11][C:10]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[O:17])=[C:9]2[CH3:29])=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.P([O-])(O)(O)=[O:35].[Na+].CC(=CC)C.Cl([O-])=O.[Na+].S([O-])(O)=O.[Na+].Cl>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH3:29])=[C:10]([C:16](=[O:17])[NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:11]=[C:12]2[CH2:13][C:14]([OH:35])=[O:15])=[C:4]([C:30]([F:32])([F:31])[F:33])[CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23665763Sodium BisulfiteHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866586531-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide

Product 1

HCID 67376656(1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acidYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of the above 1-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide (0.85 g, 1.7 mmol) in tert-butanol (14 mL)-water (3.4 mL), sodium dihydrogenphosphate (0.40 g, 2.6 mmol), 2-methyl-2-butene (0.77 mL, 6.8 mmol) and sodium chlorite (0.85 g, 5.1 mmol) were added, and the mixture was stirred at room temperature for 1 hour. A 10% aqueous sodium hydrogensulfite solution and 1M hydrochloric acid were added to the mixture to stop the reaction, and the mixture was extracted with dichloromethane. The obtained organic layer was washed with saturated brine, and after the solution was dried with sodium sulfate, it was filtered and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give (1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid (0.50 g, 57%).

Workup

  1. customthe reaction
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialafter the solution was dried with sodium sulfate, it
  5. filtrationwas filtered
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-07a7e13f65b74294ae61d443ba591b5e
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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