Summary.
The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AAP) – sub-products in the synthesis of O,O-dialkyl 1-(N-trifluoroacetylamino)alkylphosphonates and O,O-diethyl 1-aminoalkylphosphonates, were synthesized in two-stage transformations of 1-aminoalkylphosphonic acids including: trifluoroacetylation of 1-aminoalkylphosphonic acids (AAP) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AAP + TFAA/TFA→2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2→TFA-AAP). These intermediates 2 presented mixtures of the type of mixed anhydrides of TFAA and 1-(N-trifluoroacetylamino)alkylphosphonic, pyrophosphonic and polyphosphonic acids, which underwent rapid and quantitative conversion to corresponding TFA-AAP during treatment with an excess of water. The title acids were isolated by direct evaporation of the corresponding post-reaction mixtures, and their physicochemical proprieties, including deacylation abilities, were determined. TFA-AAP compounds can be re-converted into the starting amino acids AAP under respectively mild conditions (AAP→TFA-AAP→AAP).
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Kudzin, Z., Depczyński, R., Kudzin, M. et al. 1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties. Amino Acids 33, 663–667 (2007). https://doi.org/10.1007/s00726-006-0472-1
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DOI: https://doi.org/10.1007/s00726-006-0472-1