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Synthesis 1991; 1991(6): 490-493
DOI: 10.1055/s-1991-26503
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Studies on Organophosphorus Compounds XLVII: Acetyl Chloride - A Versatile Reagent for the Synthesis of 1-Aminoalkyl- and Amino(aryl)methylphosphonic Acid Derivatives

Chengye Yuan* , Shoujun Chen, Guohong Wang
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China
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Publication Date:
29 April 2002 (online)

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Acetyl chloride is used successfully in the synthesis of 1-aminoalkyl- and amino(aryl)methylphosphonic acid derivatives by a three-component condensation reaction involving diethyl phosphoramidate, aldehydes and diphenyl phosphite. Furthermore, in the reaction of benzyl carbamate, aldehydes and phosphorus(III) chloride, acetyl chloride facilates the formation of alkyl hydrogen 1-(benzyloxycarbonylamino)alkylphosphonates or aryl(benzyloxycarbonylamino) methylphosphonates, key intermediates in the synthesis of phosphonopeptide with a P-N bond. In comparison with other methods, the present variation affords wider scope of application including the use of some aliphatic aldehydes, fair yields and mild reaction conditions.