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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
ノート
印刷プレビュー

反応式

HRID 238961 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-07a7e13f65b74294ae61d443ba591b5e
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642640B2

反応ノート

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