1-(N-trifluoroacetylamino)alkylphosphonic acids: synthesis and properties.
The 1-(N-trifluoroacetylamino)alkylphosphonic acids (TFA-AA(P)) - 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 (AA(P)) using a trifluoroacetic anhydride/trifluoroacetic acid reagent (AA(P) + TFAA/TFA-->2) and subsequent hydrolysis of the intermediary compounds 2 into desired TFA-AA(P) (2-->TFA-AA(P)). 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-AA(P) 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-AA(P) compounds can be re-converted into the starting amino acids AA(P) under respectively mild conditions (AA(P)-->TFA-AA(P)-->AA(P)).
Kudzin
Z H
ZH
Institute of Chemistry, University of Łódź, Łódź, Poland. zhk@chemul.uni.lodz.pl
Depczyński
R
R
Kudzin
M H
MH
Luczak
J
J
Drabowicz
J
J
D000107:Acetylation; D000215:Acylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*
D063065:Organophosphonates