Hydrochloric Acid → HCID 22261871, compound

HRID 1610448Notes

Reaction equation

HRID 1610448 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:26])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22261773HCID 22261773, compound

Product 1

HCID 22261871HCID 22261871, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(6-chloro-2-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (4.1 g, 10.7 mmol) in methanol (20 ml) was added 2N aqueous sodium hydroxide solution (10.7 ml, 21.4 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate was added to adjust the pH to 8, and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give 3-(6-chloro-2-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (3.3 g, 86%, (2RS,3RS) form: (2RS,3SR) form=1:1).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-2900413d603d47ab94801378b5dcfc94
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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