Ethyl Acetate → L-Phenylalanine

HRID 65321

Reaction equation

HRID 65321 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-a1998eaeb8504d398dcc88c0ffe4372b
Source dataset
uspto-grants-1986_09
Patent number
US04613691

Linked notes

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