Question

Devise a synthesis of threonine from diethyl acetamidomalonate.

Short answer

Threonine comes under the category of essential amino acids. It is employed in protein biosynthesis. Some food comprising threonine include lentils and cheese.

Step-by-step solution

Threonine

Threonine comes under the category of essential amino acids. It is employed in protein biosynthesis. Some food comprising threonine include lentils and cheese.

Diethyl acetamidomalonate

Diethyl acetamidomalonate is employed for various purposes.Several pharmaceutical compounds can be created from diethyl acetamidomalonate

Synthesis of threonine from diethyl acetamidomalonate

In the first step, the diethyl acetamidomalonate is treated with sodium ethoxide. This leads to deprotonation of diethyl acetamidomalonate, forming an enolate ion. Alkylation is done with the help of methyl chloride.

This compound is heated in aqueous acid, which results in hydrolysis and decarboxylation, leading to the product threonine.