3-(4-Benzyloxyphenyl)-(S)-2-ethoxypropanoic acid ethyl ester → Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 432078

Reaction equation

HRID 432078 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[C@@H:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 110995143-(4-Benzyloxyphenyl)-(S)-2-ethoxypropanoic acid ethyl ester

Product 1

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Benzyloxyphenyl)-(S)-2-ethoxypropanoic acid ethyl ester was hydrogenated at atmospheric pressure for 2 hours in ethyl acetate using Pd/C as catalyst. Purification by chromatography on silica gel using toluen:ethyl acetate as eluant gave 3.83 g (yield in 3 steps 76%) of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester.

Workup

  1. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-ca88f86003e6446093eab14191cfa5ce
Source dataset
uspto-grants-2003_12
Patent number
US06660879B2

Linked notes

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