1206464-06-3Relevant academic research and scientific papers
A novel synthesis of 1-aminoalkanephosphonic acid derivatives from 1-(N-acylamino)-alkyltriphenylphosphonium salts
Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Kononienko, Alicja
scheme or table, p. 1986 - 1992 (2010/11/18)
Efficient and convenient procedures for the -amidoalkylation of trialkylphosphites with 1-(N-acylamino)alkyltriphenylphosphonium salts followed by a Michaelis-Arbuzov-type reaction to afford 1-(N-acylamino)alkanephosphonic acid esters have been developed.
N-Acyl-α-triphenylphosphonio-α-amino acids: Synthesis and decarboxylation toα-(N-Acylamino)alkyltriphenylphosphonium salts
Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Grymel, Mirosawa
experimental part, p. 1017 - 1027 (2009/12/07)
4-Phosphoranylidene-5(4H)-oxazolones 1 undergo hydrolysis in THF in the presence of HBF4 at room temperature to give N-acyl-α- triphenyphosphonioglycines 3 (R2 = H) in very good yields. 4-Alkyl-4- triphenylphosphonio-5(4H)-oxazolones 2 react with water in CH2Cl 2/THF solution without any acidic catalyst at 0-5°C in a few days yielding N-acyl-α-triphenylphosphonio-α-amino acids 3 (R 2 = Me) or α-(N-acylamino)alkyltriphenylphosphonium salts 4 (R2 = alkyl, other then Me).-Triphenylphosphonio-α-amino acids 3 upon heating to 105-115°C under reduced pressure (5 mm Hg) or upon treatment with a Hunig base in CH2Cl2 at 20°C undergo decarboxylation to give the corresponding α-(N-acylamino)-alkyltriphenylphosphonium salts 4, usually in very good yields.
