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

HRID 351500Notes

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].P([O-])([O-])([O-])=O.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

Reactant 3

HCID 175Acetate

HCID 1061Phosphate

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

Procedure

Ethyl (2RS) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate (0.5 ml of a solution containing 2 mg/ml in a phosphate, pH 7; 0.1M, or acetate buffer, pH 5; 0.1 M) was added to the reaction vessel followed by an enzyme (0.5 ml enzyme solution). The reaction mixture was shaken at room temperature and analysed at different times (maximum 36 h). The reaction mixture was analysed without work up by the gradient HPLC method 1 and by chiral HPLC methods 2 and 5.

Workup

addition0.1 M) was added to the reaction vessel
customanalysed at different times (maximum 36 h)

Sources & evidence

ORD record: ord-efaea4a4bad34ef09f44cf60c8d627dd
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743608B2

Reaction notes

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