5183-27-7Relevant academic research and scientific papers
PHOSPHORUS-CONTAINING AMINOCARBOXYLIC ACIDS. 1. METHOD OF PREPARATION OF PHOSPHONATE-TYPE COMPOUNDS
Ragulin, V. V.,Bofanova, M. E.,Tsvetkov, E. N.
, p. 2377 - 2382 (1989)
A method is described for the synthesis of phosphorus-containing amino carboxylic acids, by the Michaelis-Bekker or Arbuzov phosphorylation of ω-haloalkylacetamidomalonic ester.The latter were obtained by alkylating the sodium salt of acetamidomalonic ester with an excess of the α,ω-dihaloalkane.Acid hydrolysis of the phosphorus-containing alkylacetamidomalonic esters gave the required compounds.
SYNTHESE D'ACIDES ω-AMINO-ω-CARBOXY-ALKYLPHOSPHONIQUES
Aboujaoude, E. Elia,Collignon, N.,Savignac, P.,Bensoam, J.
, p. 93 - 104 (2007/10/02)
ω-Amino ω-carboxyalkylphosphonic acids 1 synthesis is reviewed.For n = 4, 5, 6 a general, efficient and inexpensive synthesis is described; acetamido(ω-bromoalkyl)malonates 12 are prepared from commercial dibromoalkanes and acetamidomalonate using the phase transfer catalysis process, then condensed with triethylphosphite through an Arbuzov reaction.An acid hydrolysis followed by purification on Dowex gives aminophosphonic acids 1 (n = 4, 5, 6) with a 70percent overall yield.The lower acid 1 (n = 2) is obtained with an identical overall yield from acetamidomalonate and 2-haloethylphosphonate using also liquid-solid phase transfer catalysis.
