Ethyl Acetate → 2-[2-(2-Carboxy methoxy-ethoxy)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([NH:14][C:15](=[O:32])[CH2:16][O:17][CH2:18][CH:19]([O:30][CH3:31])C(OCC1C=CC=CC=1)=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[C:34]([O:37]CC)(=[O:36])C>[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([NH:14][C:15](=[O:32])[CH2:16][O:17][CH2:18][CH2:19][O:30][CH2:31][C:34]([OH:37])=[O:36])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 47.5 °C
Procedure
2-[2-(2-Benzyloxy carbonyl methoxy-ethoxy)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (5 g) was dissolved in ethyl acetate (200 ml) in a pressure vessel. Palladium on carbon (5%, 50% wet, 2 g) was added and the mixture was stirred under an atmosphere of hydrogen (6 kg) for 9 hours at a temperature of 45-50° C. The catalyst was removed by filtration and distilled off ethyl acetate and the residue was washed with Diisopropyl ether and solvents residue was removed by applying high vacuum to get pure 2-[2-(2-Carboxy methoxy-ethoxy)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (2.2 g) as light yellow syrup. The product was characterized by 1H NMR which showed the presence of some impurities and hence was purified by column chromatography.
Workup
- customThe catalyst was removed by filtration
- distillationdistilled off ethyl acetate
- washthe residue was washed with Diisopropyl ether and solvents residue
- customwas removed
Sources & evidence
- ORD record
- ord-c2ad93582933476d98f1f85d523bbdc3
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012677B2
Reaction notes
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