Question

Question: Draw a stepwise mechanism for the following reaction, a key step in the synthesis of linezolid, an antibacterial agent.

Short answer

Answer

Step-by-step solution

Step-by-Step SolutionStep 1: Reaction with organolithium reagents

The polar organometallic compounds with a carbon-lithium bond, which are very strong bases, are called organolithium reagents. These transfer the organic group to the reacting compounds via deprotonation or nucleophilic addition reactions.

The 3-fluoro-4-morpholino phenyl carbamate is deprotonated in the presence of the organolithium reagent.

Deprotonation in the presence of RLi

Nucleophilic addition

The lone pair of electrons on the nitrogen atom attacks the electrophilic center, forming a C-N bond as the electrons shift towards the electronegative oxygen atom. The lone pair of electrons on oxygen attacks the carbonyl carbon resulting in ring closure to form the required antibacterial agent.