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

HRID 741536Notes

Reaction equation

HRID 741536 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-08be525f4b31445d8ec501594fc0d577
Source dataset
uspto-grants-1996_09
Patent number
US05552317

Reaction notes

Loading…