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

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Reaction Steps

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).

Provenance & Evidence