Phosphate → Methyl 2-amino-4-phenylbutanoate

HRID 741537Notes

Reaction equation

HRID 741537 reaction equation
P([O-])([O-])([O-])=O.[CH3:6]O.Cl(O)(=O)(=O)=O.[NH2:13][C@@H:14]([C:23]([OH:25])=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:6][O:24][C:23](=[O:25])[CH:14]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:13]

Participants

4

Reactant 3

HCID 1061PhosphateHCID 6950302D-HomophenylalanineHCID 86749777Methanol perchloric acid2×

Product 1

HCID 10856340Methyl 2-amino-4-phenylbutanoate

Procedure

In Example 30, a 20 g/l solution of DL-homophenylalanine methyl ester was prepared in a 0.2M phosphate buffer (pH 7.0). Then 10 g/l of a porcine pancreas lipase Sigma 3126 was also added. The mixture was caused to react at 30° C. The reaction conversion was measured by HPLC using an RP-18 column with a mobile phase consisting of 40:60 methanol/perchloric acid (pH 1.7) at an elution rate of 0.6 ml/min. The concentration of the eluent was detected at a wavelength of 215 nm. The optical purity of the product was measured using the CR(+) column with a mobile phase containing 15:85 methanol/perchloric acid (pH 1.7), at an elution rate of 0.7 ml/min. The concentration of the eluent was detected at the same wavelength of 215 nm. After 120 minutes, the reaction conversion was measured to be at 61.5%, and the e.e. value for the D-homophenylalanine and its methyl ester was measured to be 94.4%.

Workup

  1. additionwas also added
  2. customto react at 30° C

Sources & evidence

ORD record
ord-4ffb579cc7664973997a3088e677b188
Source dataset
uspto-grants-1996_09
Patent number
US05552317

Reaction notes

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