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Chapter 22: Q85. (page 923)

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

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01

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

02

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.

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Most popular questions from this chapter

Draw the product formed when the α,β-unsaturated ketone A is treated with each reagent.

(a) NaBH4, CH3OH

(b) H2 (1 equiv), Pd-C

(c) H2 (excess), Pd-C

(d) [1] CH3Li ; [2]H2O

(e) [1] CH3CH2MgBr ; [2]H2O

(f) [1] (CH2=CH2)2; [2]H2O

Draw the product formed when (CH3CH2CH2CH2)2CuLi is treated with each compound. In some cases, no reaction occurs.

a.

b.

c.

, then H2O

d.

, then H2O

What carbonyl compound and CBS reagent are needed to prepare X, an

intermediate in the synthesis of ezetimibe (trade name Zetia), a drug that lowers cholesterol levels by inhibiting its absorption in the intestines.

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