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Hydrochloric Acid → (3R)-1-(4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylic acid

HRID 1520254
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HRID 1520254 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]3[CH:40]=[CH:39][C:25]([C:26]([N:28]4[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]([O:36]CC)=[O:35])[CH2:29]4)=[O:27])=[CH:24][CH:23]=3)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:10]([CH3:41])[CH:9]=2)=[N:6][CH:7]=1.C(O)C.[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]3[CH:40]=[CH:39][C:25]([C:26]([N:28]4[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]([OH:36])=[O:35])[CH2:29]4)=[O:27])=[CH:24][CH:23]=3)[CH2:15][CH2:16][C:17]([F:19])([F:18])[F:20])=[C:10]([CH3:41])[CH:9]=2)=[N:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 131733099ethyl (3R)-1-(4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylate

생성물 1

HCID 71748058(3R)-1-(4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylic acid
수율 77.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a reaction mixture of ethyl (3R)-1-(4-((1-(4-(5-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylate (8.88 g), ethanol (30 mL) and tetrahydrofuran (30 mL) was added 1M aqueous sodium hydroxide solution (30.2 ml) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with 1M hydrochloric acid at 0° C., and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with ethyl acetate/diisopropyl ether to give the title compound (6.52 g) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with ethyl acetate/diisopropyl ether

출처 및 근거

ORD 기록
ord-a9b88b9971344fddab01eb4ca865667e
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073864B2

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