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Hydrochloric Acid → (3R)-1-(4-((4,4,4-trifluoro-1-(2-methyl-4-(5-(trifluoromethyl)pyrimidin-2-yl)phenyl)butyl)amino)benzoyl)piperidine-3-carboxylic acid

HRID 1520258
Notes
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Reaction equation

HRID 1520258 reaction equation
[F:1][C:2]([F:44])([F:43])[CH2:3][CH2:4][CH:5]([NH:23][C:24]1[CH:42]=[CH:41][C:27]([C:28]([N:30]2[CH2:35][CH2:34][CH2:33][C@@H:32]([C:36]([O:38]CC)=[O:37])[CH2:31]2)=[O:29])=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:8][C:7]=1[CH3:22].C(O)C.[OH-].[Na+].Cl>O1CCCC1>[F:44][C:2]([F:1])([F:43])[CH2:3][CH2:4][CH:5]([NH:23][C:24]1[CH:42]=[CH:41][C:27]([C:28]([N:30]2[CH2:35][CH2:34][CH2:33][C@@H:32]([C:36]([OH:38])=[O:37])[CH2:31]2)=[O:29])=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][N:13]=2)=[CH:8][C:7]=1[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 131733100ethyl (3R)-1-(4-((4,4,4-trifluoro-1-(2-methyl-4-(5-(trifluoromethyl)pyrimidin-2-yl)phenyl)butyl)amino)benzoyl)piperidine-3-carboxylate

Product 1

HCID 71767732(3R)-1-(4-((4,4,4-trifluoro-1-(2-methyl-4-(5-(trifluoromethyl)pyrimidin-2-yl)phenyl)butyl)amino)benzoyl)piperidine-3-carboxylic acid
Yield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a reaction mixture of ethyl (3R)-1-(4-((4,4,4-trifluoro-1-(2-methyl-4-(5-(trifluoromethyl)pyrimidin-2-yl)phenyl)butyl)amino)benzoyl)piperidine-3-carboxylate (4.96 g), ethanol (16 ml) and tetrahydrofuran (16 mL) was added 1M aqueous sodium hydroxide solution (15.9 mL) at 0° C., and the mixture was stirred at room temperature overnight. 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 crystallized from ethyl acetate/diisopropyl ether to give the title compound (4.37 g) as a white solid.

Workup

  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. customthe residue was crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-11fea8927700414fb7a45dfed7a95f52
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073864B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes