Sodium Hydroxide → HCID 22261691, compound

HRID 1610772Notes

Reaction equation

HRID 1610772 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:28])([F:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:29])[CH:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:28])([F:27])[C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:20][CH:21]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593315HCID 86593315, compound

Product 1

HCID 22261691HCID 22261691, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

To a solution of ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(1,1-difluoro-2,2-dimethylpropyl)benzyl]propionate (5.88 g, 13.8 mmol) in tetrahydrofuran-ethanol (30 ml—30 ml) was added 1N sodium hydroxide (28 ml, 28 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. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(1,1-difluoro-2,2-dimethylpropyl)benzyl]propionic acid (4.24 g, 77%) as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a795a6c6b222443298f722d7a02c1284
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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