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

HRID 1650901Notes

Reaction equation

HRID 1650901 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.CC(O)=O>[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 23350293Acetic acid sulfuric acid

Product 1

HCID 37697262-[(1-ethoxycarbonyl-3-phenyl-propyl)amino]propanoic AcidYield 65.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

There was dissolved 0.4 g of ethyl-α-(1-carboxyethyl)amino-γ-oxo-γ-phenylbutyrate prepared in Example 10 into 8.0 ml of 1.6% (v/v) H2SO4 -AcOH, to which 0.1 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, to which 2.5 ml of 1N NaOH solution was added and the resultant was concentrated under reduced pressure. After the residue was dissolved in water, the solution was adjusted to pH 3.0 and extracted with dichloromethane, the organic layer being washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give 0.25 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, to which 2.5 ml of 1N NaOH solution
  5. additionwas added
  6. concentrationthe resultant was concentrated under reduced pressure
  7. dissolutionAfter the residue was dissolved in water
  8. extractionextracted with dichloromethane
  9. washthe organic layer being washed with a saturated sodium chloride solution
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-f456c6094c9143b9b7004925dfb40b15
Source dataset
uspto-grants-1990_05
Patent number
US04925969

Reaction notes

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