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

HRID 238961
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HRID 238961 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-07a7e13f65b74294ae61d443ba591b5e
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642640B2

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