A Novel Synthesis of 1-Aminoalkanephosphonic Acid Derivatives from 1-(N-Acylamino)- alkyltriphenylphosphonium Salts

Abstract

Efficient and convenient procedures for the α-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. High yields and simple isolation and purification protocols are the main advantages of this method.

Keywords:

• 1-(N-Acylamino)alkanephosphonic acid esters
• 1-(N-acylamino)alkyltriphenyl- phosphonium salts
• α-amidoalkylation
• Michaelis–Arbuzov rearrangement
• phosphorus mimetics of α-amino acids

Acknowledgments

The financial help of the Ministry of Science and Higher Education of Poland (Grant No. N N204 238334) is gratefully acknowledged.

Notes

^a Mp: 109–110°C.¹⁵

^b The synthesis was carried out in a microwave reactor.

^c Mp: 37–38°C.⁴

^d The oily substance, solidifying in a refrigerator at about 0°C and melting at room temperature.