Ethyl-alpha-(1-carboxyethyl)amino-gamma-oxo-gamma-phenylbutyrate → 2-[(1-ethoxycarbonyl-3-phenyl-propyl)amino]propanoic Acid

HRID 1650902Notes

Reaction equation

HRID 1650902 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:15][CH:16]([C:18]([OH:20])=[O:19])[CH3:17])[CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].OS(O)(=O)=O.CCO>[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:15][CH:16]([C:18]([OH:20])=[O:19])[CH3:17])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 13216874Ethyl-alpha-(1-carboxyethyl)amino-gamma-oxo-gamma-phenylbutyrateHCID 73950302Sulphuric acid ethanol

Product 1

HCID 37697262-[(1-ethoxycarbonyl-3-phenyl-propyl)amino]propanoic AcidYield 79.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

There was dissolved 0.20 g of ethyl-α-(1-carboxyethyl)amino-γ-oxo-γ-phenylbutyrate prepared in Example 10 into 11.0 ml of 1% (v/v) H2SO4 -EtOH, to which 0.05 g of 10% Pd/C was added and the hydrogenation reaction was carried out at room temperature under atmospheric pressure. After completion of the reaction, the catalyst was filtered off with suction and the ethanol solution was neutralized with sodium hydroxide, followed by distillation of the solvent under reduced pressure. The residue was dissolved in water and extracted with dichloromethane, the organic layer being concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give 0.152 g of ethyl-α-(1-carboxyethyl)amino-γ-phenylbutyrate ((αS,1S)-form/(αR,1S)-form=99/1).

Workup

  1. customthe hydrogenation reaction
  2. customwas carried out at room temperature under atmospheric pressure
  3. customAfter completion of the reaction
  4. filtrationthe catalyst was filtered off with suction
  5. distillationfollowed by distillation of the solvent under reduced pressure
  6. dissolutionThe residue was dissolved in water
  7. extractionextracted with dichloromethane
  8. concentrationthe organic layer being concentrated under reduced pressure
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-110bc220289e405097d078bb2c3ec1fb
Source dataset
uspto-grants-1990_05
Patent number
US04925969

Reaction notes

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