Hydrochloric Acid → (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid

HRID 1610422Notes

Reaction equation

HRID 1610422 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([OH:24])[CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:8]([O:10]CC)=[O:9])=[CH:2]1.[OH-].[Na+].Cl>CO>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([OH:24])[CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][CH:15]=2)[C:8]([OH:10])=[O:9])=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593246ethyl (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate

Product 1

HCID 22261857(2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (19.0 g, 55.5 mmol) in methanol (100 ml) was added 2N aqueous sodium hydroxide solution (55.5 ml, 111 mmol) and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and 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 (2RS,3RS)-3-(3-furanyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (15.1 g, 86%).

Workup

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

Sources & evidence

ORD record
ord-6519338c72fa44c6a606c992e7eca6c1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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