Lefamulin synthesis
- Product Name:Lefamulin
- CAS Number:1061337-51-6
- Molecular formula:C28H45NO5S
- Molecular Weight:507.73
Reference: Heilmayer, Werner; Mang, Rosemarie; Badegruber, Rudolf; Stickmann, Dirk; Novak, Rodger; Ferencic, Mathias; Bulusu, Atchyuta Rama Chandra Murty. Synthesis of pleuromutilin derivatives for the treatment of diseases mediated by microbes. MX 2010009451. (2012).
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Yield:-
Steps:
Multi-step reaction with 7 steps
1.1: triethylamine; diphenyl phosphoryl azide / toluene / 0.58 h / 20 - 95 °C / Reflux
2.1: copper(l) chloride / 0.83 h / 80 - 100 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 15 - 40 °C / Industry scale
4.1: tetrabutyl-ammonium chloride / toluene / 4 h / 30 - 45 °C / Industry scale
5.1: hydrazine hydrate; DL-dithiothreitol / dichloromethane / 3 h / 18 - 22 °C / Industry scale
6.1: sodium hydroxide / benzyltri(n-butyl)ammonium chloride / water; tert-butyl methyl ether / 3 h / 17 - 23 °C / Industry scale
7.1: phosphoric acid / isopropyl alcohol / 16 h / 50 °C / Industry scale
7.2: 1.5 h / 0 - 25 °C / Industry scale
References:
NABRIVA THERAPEUTICS AG;RIEDL, Rosemarie;HEILMAYER, Werner;SPENCE, Lee WO2011/146954, 2011, A1
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