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

HRID 1520254Notes

Reaction equation

HRID 1520254 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

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. washthe residue was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-a9b88b9971344fddab01eb4ca865667e
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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