Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (11): 1240-1245.DOI: 10.11944/j.issn.1000-0518.2015.11.150081

• Full Papers • Previous Articles     Next Articles

A New Synthetic Route Toward Tedizolid Phosphate

ZHU Yizhong(),ZHANG Xiquan,LIU Fei,GU Hongmei   

  1. Chia Tai Tianqing Pharmaceutical Co. Ltd.,Nanjing 210042,China
  • Received:2015-03-16 Accepted:2015-08-17 Published:2015-11-02 Online:2015-11-02
  • Contact: ZHU Yizhong
  • Supported by:
    Supported by Jiangsu Postdoctoral Grant(No.1101152C)

Abstract:

Tedizolid with a yield of 82.9% was synthesized by the Suzuki coupling reaction of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine and (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-2-oxazolidinone which was prepared from bis(pinacolato)diboron using 1,1'-bis(diphenylphosphino)ferrocene-palladium(Ⅱ) dichloride dichloromethane complex as the catalyst. The effect of the catalytic system on the reaction of the borylation reaction and Suzuki reaction was investigated respectively, and the optimum reaction conditions were determined. Tedizolid phosphate was obtained by reaction of tedizolid with dibenzyl N,N-diisopropylphosphoramidite, and subsequent debenzylation with Pd/C. The total yield is 66.2%.

Key words: borides of (5R)-(bromo-fluorophenyl)-(hydroxymethyl)-oxazolidin-one, bromo-(methyl-2H-tetrazol-yl)pyridine, dibenzyl N, N-diisopropylphosphoramidite, tedizolid phosphate