Sulfuric Acid → L-Phenylalanine, methyl ester

HRID 1464454Notes

Reaction equation

HRID 1464454 reaction equation
S(=O)(=O)(O)O.[NH2:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:18](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:18][O:16][C:15](=[O:17])[C@H:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6140L-PhenylalanineHCID 10340Sodium Carbonate

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 10.2 liters of methanol and 335 ml of conc. sulfuric acid was added 1050 g of L-phenylalanine. The mixture was stirred at 90° C. for 5 hours to effect esterification. The reaction solution was adjusted with 15% sodium carbonate aqueous solution to a Ph of 7. L-Phenylalanine methyl ester was extracted with toluene to give 10.7 liters of toluene solution of L-phenylalanine methyl ester.

Workup

  1. extractionL-Phenylalanine methyl ester was extracted with toluene

Sources & evidence

ORD record
ord-9270453cffd74ebd8e66d87672cd6093
Source dataset
uspto-grants-1994_04
Patent number
US05304671

Reaction notes

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