174649-08-2Relevant academic research and scientific papers
Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation
Narina, Srinivasarao V.,Sudalai, Arumugam
, p. 6799 - 6802 (2007/10/03)
An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using d-proline-catalyzed asymmetric α-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis.
Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents
Schaus, Scott E.,Jacobsen, Eric N.
, p. 7937 - 7940 (2007/10/03)
The dynamic kinetic resolution of racemic epichlorohydrin has been achieved via enantioselective asymmetric ring opening with TMSN3 catalyzed by the (salen)Cr(III)N3 complex 1. The resulting 3-azido-1-chloro-2-trimethylsiloxypropane product was obtained in high enantiomeric purity and incorporated into the synthesis of U-100592, a representative from a class of highly-promising aryl oxazolidinone antibacterial agents.
Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.
Brickner, Steven J.,Hutchinson, Douglas K.,Barbachyn, Michael R.,Manninen, Peter R.,Ulanowicz, Debra A.,et al.
, p. 673 - 679 (2007/10/03)
Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones.
