Chapter 26.SE, Problem 39AP

Interpretation Introduction

Interpretation:

How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide is to be shown.

Concept introduction:

The steps involved in the synthesis of leucine by acetamidomalonate method are i) Conversion of the diethyl acetamidomalonate to an enolate ion by treatment with a base ii) SN² alkylation with a primary alkyl halide iii) Hydrolysis of the amide protecting group and ester groups by warming the alkylated product with aqueous acids.

The reaction can also be carried out using formaldehyde instead of an alkyl halide.

To give:

How to synthesize serine by a simple variation of amidomalonate method using formaldehyde instead of an alkyl halide.