Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate → (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic Acid Ethyl (2R)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 351522Notes

Reaction equation

HRID 351522 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][CH2:8][CH3:9])=[O:6])[CH3:2]>C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.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].[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]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

3

Reactant 1

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

Product 1

HCID 86587058(2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic Acid Ethyl (2R)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 21226156Citrate phosphateSolvent

Procedure

To ethyl (2RS) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (2.5 mg) in citrate-phosphate buffer 0.1M pH 5 (400 μl) was added the Protease 2 (or Aspergillopepsin I) from Aspergillus aculeatus expressed in Aspergillus oryzae also containing secreted enzymes from Aspergillus oryzae (WO95/02044; Handbook of Proteolytic Enzymes, Barrett, Rawlings, and Woessner Eds., 1998, Academic Press ref.1 chap. 294) (100 μl, 1 mg protein/ml final concentration). The reaction mixture was shaken at the temperatures indicated below and analysed at different times. The reaction mixture was analysed by the gradient HPLC method 1 and by the chiral HPLC method 5.

Workup

  1. additionalso containing
  2. concentrationconcentration)

Sources & evidence

ORD record
ord-e7ebb27f6d5948319e91aa534e4591dd
Source dataset
uspto-grants-2004_06
Patent number
US06743608B2

Reaction notes

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