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

HRID 351507Notes

Reaction equation

HRID 351507 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].CO>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

4

Reactant 2

HCID 887MethanolHCID 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 1061PhosphateSolvent

Procedure

Ethyl (2RS) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (0.5 g) was shaken with 60 mg of the lyophilised hydrolytic enzyme mixture from Aspergillus oryzae in 1 ml 1M phosphate buffer (pH=7) with organic co-solvents (according to the table below) at 27° C. The reaction mixture was poured into 20 ml MeOH after 4 h to stop the enzymatic reactions followed by analysis by the chiral CCE method 2.

Workup

  1. customat 27° C

Sources & evidence

ORD record
ord-ce2c95651c84422fa7fe0c4fca49d66a
Source dataset
uspto-grants-2004_06
Patent number
US06743608B2

Reaction notes

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