Sodium Hydroxide → (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid

HRID 8562Notes

Reaction equation

HRID 8562 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>P([O-])([O-])([O-])=O>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 9837207(2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acidYield 40.8%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Ethyl (2R/S) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (5 g) was added to an aqueous 0.1 M phosphate buffer pH 7 (10 ml). 100 mg of the lyophilised esterase preparation from Aspergillus oryzae was added and the mixture was stirred for 18 hours at room temperature. During that time, the pH of the reaction mixture was kept constant at pH=6-8 by addition of NaOH. Most of the water was evaporated in vacuo. Methanol was added to the remaining slurry in order to stop the hydrolysis. The precipitate, which formed was filtered off and the methanol was evaporated in vacuo. The remaining oil was dissolved in water followed by extraction of unreacted ester with tert-butyl methyl ether (TBME) (eeester=87%, determined as in Example 2). The water phase was acidified to pH=3 and the acid extracted with TBME. After drying over Na2SO4 and evaporation of the TBME, 1.8 g (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid was obtained as an oil, which crystallized on standing (m.p.=105° C., eeacid=>99%, determined as in Example 2).

Workup

  1. custom100 mg of the lyophilised esterase preparation from Aspergillus oryzae
  2. additionwas added
  3. customMost of the water was evaporated in vacuo
  4. additionMethanol was added to the remaining slurry in order
  5. customthe hydrolysis
  6. customThe precipitate, which formed
  7. filtrationwas filtered off
  8. customthe methanol was evaporated in vacuo
  9. dissolutionThe remaining oil was dissolved in water
  10. extractionfollowed by extraction of unreacted ester with tert-butyl methyl ether (TBME) (eeester=87%, determined as in Example 2)
  11. extractionthe acid extracted with TBME
  12. dry with materialAfter drying over Na2SO4 and evaporation of the TBME

Sources & evidence

ORD record
ord-89b17b9dd0da4212841faec9d0e20031
Source dataset
uspto-grants-2006_08
Patent number
US07091023B2

Reaction notes

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