625093-98-3Relevant academic research and scientific papers
Synthesis of the First Stable Phosphonamide Transition State Analogue
De Medina,Ingrassia,Mulliez
, p. 8424 - 8430 (2007/10/03)
Three methods were selected for the one-pot synthesis of the fully protected β-fluoroaminophosphonic acids, using the readily accessible N-protected β-fluoroaminals. These were activated by acylation leading, by β-elimination, to a transient N-acylimine immediately trapped by reactive forms of dialkyl phosphites. Avoiding basic conditions, the complete or partial deprotection of these N-protected β-fluoroaminophosphonic esters allowed the synthesis of the free amino acids, their esters, and a racemic β-trifluorophosphonamidic acid. The latter, which represents a transition state analogue formed by the bacterial transpeptidase, is perfectly stable at pH 4.7, contrary to the nonfluorinated compounds.
