Synthesis and Mass Spectrometry of 2-Hydroxyethyl 1-Aminoalkylphosphonates

Abstract

Mannich-type condensation of benzyl carbamate, aldehydes, and chlorophosphite has been widely used in the synthesis of 1-(N-benzyloxycarbonylamino)arylmethyl-phosphonic derivatives. Reactions of benzyl carbamate, aldehydes, and cyclic chlorophosphite 2-chloro-1,3,2-dioxaphospholane were conducted in benzene to afford a mixture of benzyl [(2-oxido-1,3,2-dioxaphospholane-2-yl)arylmethyl]-carbamates and 2-hydroxyethyl 1-(N-benzoxycarbonylamino)arylmethylphos-phonate monoesters. 2-hydroxyethyl 1-(N-benzoxycarbonylamino)arylmethylphos-phonate monoesters were obtained exclusively after the addition of water under stirring. The reaction mechanism was discussed. Their mass spectrometric fragmentations were also described.

Keywords:

• Alkylphosphonate
• amino acid
• aminoalkylphosphonic acid
• Mannich-type reaction
• mass spectrometry
• multiple component condensation
• synthesis

Acknowledgments

This work was supported in part by the National Natural Science Foundation of China (Project No. 20472005), Ministry of Education of China (Scientific Research Foundation for the Returned Oversea Chinese Scholars), Peking University, and Tsinghua University, Beiging, China.