Bergmann azlactone peptide synthesis

The Bergmann azlactone peptide synthesis is a classic organic synthesis process for the preparation of dipeptides.

In the presence of a base, peptides are formed by aminolysis of N-carboxyanhydrides of amino acids with amino acid esters (1).

 

 

 

 

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This reaction can be looked at in further detail by Bailey.

The resulting peptide is then protected by esters of benzylchroroformate in order to keep the amino groups intact (2).

${\displaystyle {\begin{matrix}{}\\{\ce {{C6H5CH2OCOCl}+H2N{\underset {| \atop \displaystyle R}{C}}HCOOR'->[{\ce {NaOH}}^{*};\;0-20^{\circ }{\ce {C}}][({\ce {H2O}})]C6H5CH2OCOH{\underset {| \atop \displaystyle R}{C}}HCOOR'}}\\{}\\*\ {\ce {{CHCl}+(C2H5)3N,{CH3COOC2H5}+MgO,{CHCl3}+{H2O}+Na2CO3}}\end{matrix}}}$

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