1-(N-Trifluoroacetylamino)alkylphosphonic acids: synthesis and properties

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: trifluoroacetyla...

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Bibliographic Details
Published in:Amino acids 2007-11, Vol.33 (4), p.663-667
Main Authors: Kudzin, Z. H, Depczyński, R, Kudzin, M. H, Łuczak, J, Drabowicz, J
Format: Article
Language:English
Subjects:
1-(N- Trifluoroacetylamino)alkylphosphonic acids
1-Aminoalkylphosphonic acids
Acetylation
Acylation
Amino acids
Aminophosphonic acids
Anhydrides
Conversion
Evaporation
Hydrolysis
Magnetic Resonance Spectroscopy
Mixed anhydrides
Molecular Structure
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Synthesis
Transformations
Trifluoroacetylation
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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[rightward arrow]2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AAP (2[rightward arrow]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[rightward arrow]TFA-AAP[rightward arrow]AAP).
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-006-0472-1