Sodium Hydroxide → (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid

HRID 1775770Notes

Reaction equation

HRID 1775770 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][CH2:12][C@H:13]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:14]([O:16]C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(#N)C>[CH2:1]([O:8][CH2:9][O:10][CH2:11][CH2:12][C@H:13]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131734747methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

Product 1

HCID 131734748(S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acidYield 84.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(Step 3) To methyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (190 mg, 0.52 mmol) obtained in Step 2, acetonitrile (10 mL) and an aqueous sodium hydroxide solution (0.5 mol/L, 5.2 mL, 2.58 mmol) were added, and the resulting mixture, was stirred at room temperature for 5.5 hours. To the reaction mixture, Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) was added thereto to neutralize the mixture, and the insoluble matter was removed by filtration, and then, the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, and then, the solvent was evaporated under reduced pressure, whereby (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid (156 mg) was obtained.

Workup

  1. additionTo the reaction mixture, Dowex 50 (registered trademark) (Muromachi Technos, 50WX8, 50-100 mesh, H+ form) was added
  2. customthe insoluble matter was removed by filtration
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed209b38575f4188b0289381100eea7a
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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