Process Investigations on the One-Pot Synthesis of Rifamycin S Avoiding Chlorinated Solvents

The facile synthesis of rifamycin S from rifamycin B, a member of the ansamycin family of antibiotics, via the oxidation of rifamycin B was developed. Currently on an industrial scale, this oxidation is performed using harsh pH conditions and chlorinated solvents. With the development of a suitable...

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Bibliographic Details
Published in:Organic process research & development 2015-11, Vol.19 (11), p.1544-1547
Main Authors: Löw, Sebastian A, Nestl, Bettina M, Weissenborn, Martin J, Zepeck, Ferdinand, Hauer, Bernhard
Format: Article
Language:English
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Summary:The facile synthesis of rifamycin S from rifamycin B, a member of the ansamycin family of antibiotics, via the oxidation of rifamycin B was developed. Currently on an industrial scale, this oxidation is performed using harsh pH conditions and chlorinated solvents. With the development of a suitable buffer/methanol system, a similar yield and space-time-yield in comparison to the current process can be obtained renouncing chlorinated solvents. Employment of methanol as a reaction medium in this process is crucial for attaining high yields under mild reaction conditions. With this method a space-time-yield of 189 g L–1 h–1 of rifamycin S was achieved in one step.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.5b00070