The Synthetic Routes of Tedizolid phosphate

Tedizolid phosphate is an antibiotic drug that is used to treat various bacterial infections.
The synthesis of tedizolid phosphate has been reported in several literature articles, which have described different synthetic routes for this compound.
In this article, we will discuss some of the most commonly used synthetic routes for tedizolid phosphate and their advantages and disadvantages.

One of the most common synthetic routes for tedizolid phosphate involves the condensation of 2-cyano-4-nitrophenyl acetate with 2,4-dinitrophenylhydrazine to form the intermediate nitro compound.
This intermediate is then reduced with lithium aluminum hydride (LAH) to form the corresponding amine.
The amine is then coupled with 2,4-dichlorotoluene to form the diazotized compound, which is further coupled with potassium phosphate to form the final tedizolid phosphate product.

Another synthetic route for tedizolid phosphate involves the condensation of 2-cyano-4-nitrophenyl acetate with p-toluenesulfonyl chloride to form the tosylate intermediate.
This intermediate is then treated with sodium azide to form the corresponding diazotized compound, which is further coupled with 2,4-dichlorotoluene and potassium phosphate to form the final tedizolid phosphate product.

A third synthetic route for tedizolid phosphate involves the condensation of 2-cyano-4-nitrophenyl acetate with sodium nitrite to form the nitro compound.
This nitro compound is then treated with lithium aluminum hydride to form the corresponding amine.
The amine is then treated with 2,4-dichlorotoluene and potassium phosphate to form the final tedizolid phosphate product.

Each of these synthetic routes has its own advantages and disadvantages.
For example, the first route involves the use of hazardous reagents such as lithium aluminum hydride and sodium azide.
The second route requires the isolation of the tosylate intermediate, which can be difficult to purify.
The third route involves the use of sodium nitrite, which can be expensive and difficult to handle.

Overall, the synthesis of tedizolid phosphate requires a series of steps, including the preparation of the nitro or diazotized compound, the coupling with 2,4-dichlorotoluene, and the final dephosphorylation step.
These steps can be challenging and require careful optimization to ensure product purity and yield.

One alternative approach to tedizolid phosphate synthesis involves the use of microwave-assisted synthesis.
This approach has been reported to reduce the number of steps required for synthesis and decrease the reaction time.
For example, a microwave-assisted synthesis of tedizolid phosphate has been reported using a modified Wacker process, which involves the condensation of 2-cyano-4-nitrophenyl acetate with 2,4-dichlorotoluene in the presence of potassium phosphate.
The reaction mixture is then heated in a microwave reactor for 15 minutes to complete the synthesis.
This approach has been shown to improve the yield and purity of the tedizolid phosphate product.

In conclusion, tedizolid phosphate is an important antibiotic drug that has been synthesized using a variety of synthetic routes.
While each route has its own advantages and disadvantages, alternative approaches such as microwave-assisted synthesis have been shown to improve the yield and purity of the final product.
As the demand for new antibiotics continues to grow, the development of efficient and cost-effective synthetic routes for tedizolid phosphate