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

HRID 351505Notes

Reaction equation

HRID 351505 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(#N)C>C([O-])(=O)C>[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

4

Reactant 2

HCID 6342AcetonitrileHCID 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 175AcetateSolvent2×

Procedure

Ethyl (2RS) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate 0.4 ml of a solution containing 6.25 mg/ml in acetate buffer (0.1 M, pH 5 with acetonitrile 12.5 vol. % added to the buffer) was added followed by a sample of 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) (0.1 ml of a solution containing 5 mg/ml) in an acetate buffer (0.1 M; pH=5). The reaction mixture was shaken at room temperature and analysed at different times (maximum 24 h). The reaction mixture was analysed by the gradient HPLC method 1 and by the chiral HPLC method 1.

Workup

  1. addition% added to the buffer)
  2. additionwas added
  3. additionalso containing
  4. customanalysed at different times (maximum 24 h)

Sources & evidence

ORD record
ord-af2d2a07bf0d4c27ac56e3b09caa3355
Source dataset
uspto-grants-2004_06
Patent number
US06743608B2

Reaction notes

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