Ultrasound-accelerated Synthesis of N-protected Amino Alkyl Iodides from Amino Alcohols Using P2I4 Reagent and its Application in the Synthesis of Amino Alkyl Thiols

Abstract

Introduction: Synthesis of amino acid-derived alkyl iodides results in versatile intermediates for many peptidomimetics, and hence, the approach for their synthesis under neutral conditions was achieved in the present work. Method: The N-protected amino acids were reduced to amino alcohols under T3P as an activator and NaBH4 as a reducing partner. Thus, synthesized aminols were sonicated with diphosphorus tetraiodide (P2I4) in CS2 to obtain the N-protected aminoalkyl iodides. Result: We established the utilisation of the alkyl iodides by converting them to aminoalkyl thiols, which serve as building blocks for many heterocycles and other drug candidates. The ultrasonication medium works effectively for all the intermediates preparation; the conditions are mild, and yields are almost quantitative in all steps. Conclusion: The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS analysis.