Toluene → L-Phenylalanine, methyl ester

HRID 980128Notes

Reaction equation

HRID 980128 reaction equation
[C:1]1(C)C=CC=CC=1.[OH-].[Na+].[NH2:10][C@H:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[CH3:1][O:20][C:19](=[O:21])[C@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6140L-PhenylalanineHCID 14798Sodium Hydroxide

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 0.2 molar solution phenylalanine methyl ester in 10 milliliters of water was prepared. Toluene was added and the pH of the system adjusted to 7.0 with sodium hydroxide. Chymotrypsin in the amount of 1 milligram was added. The concentration of phenylalanine in the aqueous phase was monitored. The initial concentration was 0.05 molar and the final concentration at the end of the hydrolysis was 0.15 molar, consistent with only one isomer being extracted.

Workup

  1. additionChymotrypsin in the amount of 1 milligram was added
  2. concentrationThe initial concentration was 0.05 molar and the final concentration at the end of the hydrolysis
  3. extractionconsistent with only one isomer being extracted

Sources & evidence

ORD record
ord-dc15b1b100064f8eb3205ca1a7af154c
Source dataset
uspto-grants-1987_01
Patent number
US04636470

Reaction notes

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