(S)-2-amino-4-phenylbutanoic acid → D-Homophenylalanine

HRID 741539Notes

Reaction equation

HRID 741539 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C@H:9]([NH2:13])[C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1>C(OCC)(=O)C.O>[NH2:13][C@@H:9]([C:10]([OH:12])=[O:11])[CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2724505(S)-2-amino-4-phenylbutanoic acid

Product 1

HCID 6950302D-Homophenylalanine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

After the completion of the reaction, an extractant such as ethyl acetate is added to the reaction mixture which separates the reaction mixture into an upper layer and a lower layer. The upper layer contains D-HPAE in ethyl acetate and the lower layer contains L-HPA in water. After separating the lower layer from the upper layer, the extractant, i.e., ethyl acetate, can be vaporized to obtain D-HPAE, which can be chemically hydrolyzed to obtain D-homophenylalanine. L-HPA can be separated from the lower layer by adjusting its solution pH to about 6.3 to cause the precipitation thereof.

Workup

  1. customAfter the completion of the reaction
  2. customAfter separating the lower layer from the upper layer
  3. customto obtain D-HPAE, which

Sources & evidence

ORD record
ord-b8f311a753f44843890873f1a2d01a9b
Source dataset
uspto-grants-1996_09
Patent number
US05552318

Reaction notes

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