For the given Boc-protection of phenylalanine, a mechanism needs to be drawn. Concept introduction: Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with d-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are, Nucleophilic attack to form tetrahedral intermediate Loss of leaving group to reform carbonyl Proton transfer to give protected amino acid

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Chapter 25, Problem 83PP

Interpretation Introduction

Interpretation:

For the given Boc-protection of phenylalanine, a mechanism needs to be drawn.

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with d-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

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