Hydrochloric Acid → (2RS,3RS)-3-(3,4-difluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:27])[CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:27])[CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl (2RS,3RS)-3-(3,4-difluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (9.7 g, 25.0 mmol) in methanol (40 ml) was added 2N aqueous sodium hydroxide solution (25 ml, 50.0 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 ethyl acetate-hexane to give (2RS,3RS)-3-(3,4-difluorophenyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (6.7 g, 74%).
Workup
- extractionextracted with ethyl acetate (200 ml×2)
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was recrystallized from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-e30f9ff1c36a4843b2fd2d21987eca43
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982348B2
Reaction notes
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