The oxazolidinone functional group has been shown to lead to active antibiotics. Two novel oxazolidinones were synthesized following a five step synthetic sequence. One of the oxazolidinones contains a pyrrolidine ring and the other a morpholine ring. The synthetic pathway used to create these antibiotic derivatives was accomplished by first reacting an aldehyde with a secondary amine via reductive amination before the oxazolidinone ring was formed. This eliminates the need to protect and deprotect the aldehyde group. The final products were successfully purified by a new means of triturating with diethyl ether multiple times rather than column chromatography. The synthetic route followed can now be used to make many new amine containing derivatives. The HCl salts of the products were produced by treating THF solutions of the products with HCl/Ether solutions. These salts will have increased water solubility and allow for easier drug administration.

Synthesis of tertiary amine functionalized oxazolidinones

ACS Spring 2022

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