Synthesis and antimicrobial activity of 5,5′‐dimethyl‐2‐oxido‐[1,3,2]‐dioxaphos‐phorinane‐2‐yl‐amino carboxylates

Abstract

AbstractSynthesis of several 5,5‐dimethyl‐2‐oxido‐[1,3,2]‐dioxaphosphorinane‐2‐yl‐amino carboxylates (4a–j) was accomplished through a two‐step process. This involves prior preparation of the intermediate monochloride (2), 2‐chloro‐5,5‐dimethyl [1,3,2]dioxaphosphorinane‐2‐oxide and its subsequent reaction with various amino acid esters (3a–j) in dry tetrahydrofuran in the presence of triethyl amine at room temperature. They were characterized by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectral data. Their antifungal and antibacterial activity is also evaluated. Majority of these compounds exhibited moderate antimicrobial activity in the assay. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:256–260, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20426