Ethyl Acetate → L-Phenylalanine

HRID 980127Notes

Reaction equation

HRID 980127 reaction equation
C[O:2][C:3](=[O:13])[CH:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].C(OCC)(=O)C.[OH-].[Na+]>O>[NH2:5][C@H:4]([C:3]([OH:13])=[O:2])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 75737DL-Phenylalanine, methyl ester

Product 1

HCID 6140L-PhenylalanineYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.15 grams of D,L-phenylalanine methyl ester in 2.5 milliliters of water was added to 5.0 milliliters of ethyl acetate. The pH was adjusted to 6.5 with 2.5 milliliters of sodium hydroxide. Two milligrams of chymotrypsin was added and the reaction was stirred gently at room temperature. A white precipitate appeared after 1.5 hours. The precipitate was isolated after 2 hours yielding 0.22 grams with an optical rotation equivalent to 98% pure L-phenylalanine.

Workup

  1. additionTwo milligrams of chymotrypsin was added
  2. customThe precipitate was isolated after 2 hours

Sources & evidence

ORD record
ord-adce96bf51124dc1889a948e0cd7dbe2
Source dataset
uspto-grants-1987_01
Patent number
US04636470

Reaction notes

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