A variation of the acetamidomalonate synthesis can be used to synthesize threonine. The process involves the following steps: Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1; Enolate anion 1 makes a nucleophilic attack on acetaldehyde, forming tetrahedral intermediate 2; Protonation of the oxyanion forms alcohol 3; Acid hydrolysis yields dicarboxyamino alcohol 4; Decarboxylation leads to the final amino acid. Write out the mechanism on a separate sheet of paper, and then draw the structure of enolate anion 1.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.45P
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A variation of the acetamidomalonate synthesis can be used to synthesize threonine. The process involves the following steps:

  1. Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;
  2. Enolate anion 1 makes a nucleophilic attack on acetaldehyde, forming tetrahedral intermediate 2;
  3. Protonation of the oxyanion forms alcohol 3;
  4. Acid hydrolysis yields dicarboxyamino alcohol 4;
  5. Decarboxylation leads to the final amino acid.

Write out the mechanism on a separate sheet of paper, and then draw the structure of enolate anion 1.

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