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Wednesday 2 April 2014

Ranbezolid from Ranbaxy as an oxazolidinone antibacterial

Ranbezolid structure.svg

Ranbezolid

392659-39-1 hydrochloride
392659-38-0 (free base)
N-{[(5S)-3-(3-Fluoro-4-{4-[(5-nitro-2-furyl)methyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
(S)-N-[[3-fluoro-4-[N-1[4-{2-furyl-(5-nitro)methyl}]piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]-methyl]acetamide

  • Mp: 207–209 °C.
  •  1H NMR (DMSO, 300 MHz):  
    δ 8.30 (t, 1H, –NHCO–), 
    7.75 (d, J = 3.3 Hz, 1H, furyl–H), 
    7.52 (dd, 1H, phenyl–H), 
    7.3–7.0 (m, 3H, phenyl–H, furyl–H), 
    4.70 (m, 1H, oxazolidinone ring C5H), 
    4.63 (s, 2H), 
    4.08 (t, J = 8.8 Hz, 1H, –CH2–), 
    3.73 (t, J = 7.5 Hz, 1H), 
    3.43 (br m, piperazine–H merged with H2O in DMSO), 
    .83 (s, 3H, –COCH3).
  • HPLC purity: 98%. 
    Anal. Calcd for C21H25ClN5O6·0.5H2O: C, 50.76; H, 5.48; N, 14.09. Anal. Found: C, 50.83; H, 5.17; N, 13.83.

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