Alkylation of potassium 1-(N-benzyloxycarbonyl-amino)alkylphosphonates and phosphinates in the presence of 18-crown-6

Article abstract of DOI:10.1080/00397919508015491

During past several years we have been engaged in the synthesis of phosphono peptides, peptide analogues with phosphonic acid replacing C-terminal or N-terminal carboxylate moiety. These compounds are of interest not only because of their promise of direct practical applications but also as a source of information about mechanisms of enzymatic reactions. Esters of N-blocked 1-aminoalkylphosphonic and phosphinic acids are popularly used as starting substrates in multistep syntheses of phosphono peptides. Although several methods for their preparation have been described the search for the new and useful methods of their synthesis is still in progress. In this paper we report that the use of complexes of potassium 1-(N-benzyloxycarbonylamino)alkylphosphonates and phosphinates with 18-crown-6 as nucleophiles in the reaction with alkyl halides afforded the desired esters in good yields.