An Economically Viable Process for the Synthesis of a Chiral Oxazolidinone ((S)-4-Benzyl-2-oxazolidinone) from Amino Acid

References

• Anastas , P. , and J. Warner . 2000 . Green Chemistry: Theory and Practice . New York : Oxford University Press .
   Google Scholar
• Betush , M. P. , and S. S. Murphree . 2009 . Use of chiral oxazolidinones for a multi-step synthetic laboratory module . J. Chem. Edu. 86 : 91 – 94 .
   Google Scholar
• Ella-Menye , J. R. , and G. Wang . 2007 . Synthesis of chiral 2-oxazolidinones, 2-oxazolines, and their analogs . Tetrahedron. 63 : 10034 – 10041 .
   Web of Science ®Google Scholar
• Evans , D. A. , A. Weber , and E. Weber . 1986. Asymmetric glycine enolatealdol reactions: synthesis of cyclosporin's unusual amino acid, MeBmt. J. Am. Chem. Soc. 108: 6757–6761
   Web of Science ®Google Scholar
• Gage , J. R. , and D. A. Evans . 1993 . (s)-4-(Phenylmethyl)-2-oxazolidinone . Org. Synth. 8 : 528 .
   Google Scholar
• Ghosh , A. K. , S. Leshchenko-Yashchuk , D. D. Anderson , A. Baldridge , M. Noetzel , H. B. Miller , Y. Tie , Y. F. Wang , Y. Koh , I. T. Weber , and H. Mitsuya . 2009 . Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1′-ligands to enhance backbone-binding interactions with protease: Synthesis, biological evaluation, and protein−ligand x-ray studies . J. Med. Chem. 52 : 3902 – 3914 .
   PubMedGoogle Scholar
• Hoogenboom , R. , F. Wiesbrock , and U. S. Schubert . 2005 . Microwave-assisted cationic ring-opening polymerization of a soy-based 2 oxazoline monomer . Polym. Mater. Sci. Eng. 93 : 894 – 895 .
   Google Scholar
• Juszczyk , P. , R. Kasprzykowska , and A. S. Kołodziejczyk . 2003 . Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton . Lett. Pept. Sci. 10 : 79 – 82 .
   Google Scholar
• Kottenhaim , M. , K. Drauz , and H. Hilpert . 1998 . Process for the reduction of amino acids and the derivatives thereof. U.S. Patent 5,744,611.
   Google Scholar
• Madariaga , M. G. , and S. Swindells . 2007 . Oxazolidinones and human immunodeficiency virus . Antimicrob. Agents Chemother. 51 : 1130 .
   PubMed Web of Science ®Google Scholar
• Matsuda , H. , A. Baba , R. Nomufa , M. Korl , and S. Ogawa . 1985 . Ethanol to gasoline process: Effect of variables, mechanism, and kinetics . Ind. Eng. Chem. Prod. Res. Dev. 24 : 239 – 244 .
   Google Scholar
• McKennon , M. J. , A. I. Meyers , K. Drauz , and M. Schwarm . 1993 . A convenient reduction of amino acids and their derivatives . J. Org. Chem. 58 : 3568 – 3571 .
   Web of Science ®Google Scholar
• Moellering , R. C. Jr. 2003 . Linezolid: The first oxazolidinone antimicrobial . Ann. Intern. Med. 138 : 135 – 142 .
   PubMed Web of Science ®Google Scholar
• Mukhtar , T. A. , and G. D. Wright . 2005 . Streptogramins, oxazolidinones, and other inhibitors of bacterial protein synthesis . Chem. Rev. 105 : 529 – 542 .
   PubMed Web of Science ®Google Scholar
• Philippe , M. R. , R. Tuloup , and J. L. Morancais . 1997 . Use of oxazolidinone derivatives as anti-penetrating agents in a cosmetic and/or dermatological composition. U.S. Patent, 6 , 255 – 332 .
   Google Scholar
• Pulla , S. , V. Unnikrishnan , P. Ramidi , S. Z. Sullivan , A. Ghosh , J. L. Dallas , and P. Munshi . 2011 . Interaction of substrate and catalyst during the formation of oxazolidinones from 2-aminoalcohols and diethyl carbonate using recyclable 1,3-dichlorodistannoxanes . J. Mol. Cat. A: Chem. 338 : 33 – 43 .
   Google Scholar
• Saeed Aamer and Zaman Ashraf . 2006 . Sodium borohydride reduction of aromatic carboxylic acids via methyl esters . J. Chem. Sci. 118 : 416 – 423
   Google Scholar
• Xiao , T. L. , B. Zhang , J. T. Lee , F. Hui , and D. W. Armstrong . 2001 . Reversal of enantiomeric elution order on macrocyclicglycopeptide chiral stationary phases . J. Liq. Chromatogr. 24 : 2673 – 2684 .
   Web of Science ®Google Scholar
• Yu , D. S. , L. Huang , H. Liang , and P. Gong . 2005 . A new and efficient synthetic method and antibacterial activities of oxazolidinone analogues . Chin. Chem. Lett. 16 : 875 – 878 .
   Google Scholar