EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Chapter 25.3, Problem 2LTS
Interpretation Introduction

Interpretation:

Racemic tryptophan prepared by using amidomalonate synthesis need to be shown.

Concept introduction:

Amidomalonate synthesis is a process in which a halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 25.3, Problem 2LTS

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

To describe: how tryptophan can be synthesized using amidomalonate synthesis.

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Chapter 25 Solutions

EBK ORGANIC CHEMISTRY-PRINT COMPANION (

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