Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

Abstract

A new and concise synthetic route to enantiopure Linezolid from (S)-epichlorohydrin

Author(s): T Rajesh, G Madhusudhan, K Mukkanti, S P Narayana Rao and K Kishore Babu

A new and short synthesis of Linezolid 1 has been emphasized in two path ways. The synthetic route in both the ways involves preparation of 2-((R)-3-(3-fluoro-4-morpholinophenylamino)-2- hydroxypropyl)isoindoline-1,3-dione 2 as a key intermediate starting from (S)-epichlorohydrin and phthalimide 3a. One of these methods involves the direct N-alkylation of 3-fluoro-4- morpholinobenzenamine 3b with 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione 4a. Alternatively, compound 2 was prepared by using one-pot three step sequence via 2-(((S)-oxiran- 2-yl)methyl)isoindoline-1,3-dione 4b.


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