A convenient synthesis of the antibacterial agent linezolid
Starting with 3,4-difluorobenzoic acid (8) and (S)-epichlorohydrin (13) a convergent synthesis of linezolid (1) was developed that is attractive for large scale preparation of the drug. The synthetic strategy involves a 1+3 cycloaddition reaction between the chiral epoxide 11 (prepared from 13) and isocyanate 3 (obtained from 8) that was generated in situ by a Curtius rearrangement. The resulting Schiff base precursor of linezolid (12) crystallized from the reaction mixture and was readily converted to linezolid by an acid-catalyzed hydrolysis followed by an acetylation.
McCarthy, James R.
supporting information
p. 6846 - 6847
(2015/11/27)
PROCESSES FOR PREPARING RIVAROXABAN
Processes and intermediates for preparing rivaroxaban, and analogs and derivatives thereof, and pharmaceutically acceptable salts of each of the foregoing, are described herein.
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Page/Page column 19
(2013/10/22)
PROCESSES FOR PREPARING LINEZOLID
Processes and intermediates for preparing linezolid, and pharmaceutically acceptable salts thereof, are described herein.
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Example 31
(2011/11/13)
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