A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid

Abstract

A concise and efficient synthesis of linezolid and eperezolid were accomplished through a convergent scheme utilizing diverse reaction conditions. The synthesis demonstrates utility of a new approach to facilitate the expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones and easier insertion of N-acetyl group. This new approach offers the possibility of accessing related 2-oxazolidinone members easily as well as making additional analogues of Linezolid. The adopted method afforded high purity and excellent yield compared to other existing synthetic methods. The compounds were successfully characterized by known spectroscopic techniques.

Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide

“…For example, linezolid (Zyvox®) and tedizolid (Sivextro®) among others are marketed worldwide for their unique antibacterial activity, even towards multidrug-resistant bacteria. [1][2][3][4][5] Additionally, 2-oxazolidinones are used as intermediates in organic synthesis, [6][7][8] as chiral auxiliaries [9][10][11][12][13][14][15] and in polymers. [16][17][18] Depending on the starting substrate, intermolecular synthetic routes for these cyclic urethanes may lead through aziridines, [19][20][21][22][23][24][25] propargylamines [26][27][28][29][30][31] or aminoalcohols [32][33][34][35][36][37] (Scheme 1a).…”