Sodium Hydroxide → (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid
Reaction equation
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][CH:9]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[OH:16])[C:10]([O:12]CC)=[O:11])([F:4])[CH3:3].[OH-].[Na+]>O1CCCC1CCO>[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][CH:9]([CH:15]([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[OH:16])[C:10]([OH:12])=[O:11])([F:4])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionate (5.97 g, 17.6 mmol) in tetrahydrofuran-ethanol (30 ml)-(20 ml) was added 2N sodium hydroxide (18 ml, 36 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure, and the aqueous layer was acidified with 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The filtrate was recrystallized from hexane-ethyl acetate to give (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid(4.48 g, 82%) as colorless crystals.
Workup
- customAfter completion of the reaction
- customthe organic solvent was evaporated under reduced pressure
- extractionThe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe filtrate was recrystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-f103aa0a97e247948d3ddcf6afd6e7ad
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982348B2
Reaction notes
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