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Synthesis of Linezolid and Rivaroxaban via asymmetric Henry reaction

Autoři: Vrbický Martin | Kocúrik Martin | Marek Lukáš | Pochobradský Jaroslav | Drabina Pavel

Rok: 2021

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

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Jazyk	Název	Abstrakt	Klíčová slova
eng	Synthesis of Linezolid and Rivaroxaban via asymmetric Henry reaction	Oxazolidinones belong to new class of antibiotics used for treating serious skin, bone, postoperative and other infections. They are active against large spectrum of gram-positive bacteria, including methicillin- and vancomycin-resistant staphylococci. An oxazolidinone derivative for other purposes represents Rivaroxaban, which is approved by the FDA for venous treatment and/or preventing thromboembolic diseases. Herein, we are presenting significant improvement in synthesis of antibacterial agent Linezolid, previously reported by Piccionello et al.,2 and anticoagulant drug Rivaroxaban. Both reaction sequences involve six steps overall, starting from commercially available and inexpensive materials. The stereogenic center was introduced by asymmetric Henry reaction catalyzed by the copper(II) complexes of selected chiral ligands. The use of imidazolidin-4-one or bis(oxazoline) ligands provide high yields and enantioselectivities of the chiral precursors of both drugs (up to 94%, up to 90% ee). With regard to obtained results, the most efficient catalysts and appropriate reaction conditions were selected for subsequent study, in which the carbamate functional group of starting aldehydes was modified. The influence of this structural modification on the enantioselectivity of asymmetric Henry reaction was evaluated	Linezolid; Rivaroxaban; Henry reaction; imidazolidin-4-one; bis(oxazoline)

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