Acetylphenylalanine methyl ester → L-Phenylalanine

HRID 2091436Notes

Reaction equation

HRID 2091436 reaction equation
C[O:2][C:3](=[O:16])[C@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:5]C(=O)C>Cl>[NH2:5][C@H:4]([C:3]([OH:16])=[O:2])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 704002Acetylphenylalanine methyl ester

Product 1

HCID 6140L-PhenylalanineYield 99.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
105 °C

Procedure

There was dissolved 1.40 g (6.0 mmol) of the phenylalanine methyl ester (31) in 50 ml of a 1N HCl solution and then the resulting solution was stirred at 105° C. for 12 hours. After cooling, the resulting mixture was concentrated and then ion-exchanged using Dowex-50w-X8 to thus give 1.10 mg (5.97 mmol, 99%) of the title compound: phenylalanine (1).

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting mixture was concentrated

Sources & evidence

ORD record
ord-72f89508209447509f2f76b2b3bbf3b7
Source dataset
uspto-grants-2013_05
Patent number
US08440169B2

Reaction notes

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