Water → (3S)-3-amino-3-phenylpropanoic acid

HRID 984764Notes

Reaction equation

HRID 984764 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=[O:5].O.[OH-].[Na+]>C(OC)(C)(C)C>[NH2:1][C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 236379Ethyl 3-amino-3-phenylpropanoate

Product 1

HCID 686704(3S)-3-amino-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

9.2 mmol of the racemic compound ethyl rac-3-amino-3-phenylpropionate (1.79 g) are taken up in 50 ml of a two-phase solvent mixture composed of 25 ml of water and 25 ml of methyl tert-butyl ether (MTBE) as the organic solvent component and set to a pH of 8.2 by automatic pH adjustment through adding 1 M sodium hydroxide solution (obtained through Merck). On reaching a reaction temperature of 20° C., 200 mg of lipase PS (Pseudomonas cepacia; obtained through Amano Enzymes, Inc.) are added to start the reaction. After a reaction time of 3, 5 and 24 hours, the conversion rate of the (S)-3-amino-3-phenylpropionic acid formed is determined. A conversion of 23.5% after 3 hours or a quantitative conversion of approximately 50% after 15 hours and an enantioselectivity of 89.0% ee (after 15 hours) are determined. The conversion and enantioselectivity are determined by means of HPLC.

Workup

  1. customa reaction temperature of 20° C., 200 mg of lipase PS (Pseudomonas cepacia; obtained through Amano Enzymes, Inc.)
  2. additionare added
  3. customthe reaction

Sources & evidence

ORD record
ord-292b4544445a4eb8a019c37baaa39fe7
Source dataset
uspto-grants-2005_03
Patent number
US06869781B2

Reaction notes

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