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Introduction
Ethyl 6-(tert-butyl)-3-cyano-2-hydroxyisonicotinate (EBCH) is an important intermediate in the synthesis of active pharmaceutical ingredients (APIs) and agricultural chemicals.
It has also found application as a catalyst in the production of polyurethane polymers.
The synthetic routes of EBCH can be broadly classified into three categories: classical synthesis, modern synthesis, and biotechnological synthesis.
In this article, we will discuss the different synthetic routes of EBCH and highlight their significance in the chemical industry.
Classical Synthesis of EBCH
Classical synthesis of EBCH involves the use of traditional methods, such as chemical reduction, alkylation, and condensation reactions.
One of the most common methods of classical synthesis of EBCH is the reduction of 6-bromo-2-oxo-1,2-oxazolidin-3-one using lithium aluminum hydride (LiAlH4) in the presence of a polar solvent, such as acetonitrile or DMF.
The resulting 6-(tert-butyl)-2-oxo-1,2-oxazolidin-3-one can then be treated with sodium bis(2-hydroxyethyl) sulfite to produce EBCH.
The classical synthesis of EBCH has several advantages, such as the availability of cheap and readily available reagents, the ease of scaling up the reaction, and the low level of hazard associated with the reaction.
However, this method also has several disadvantages, such as the generation of hazardous byproducts, the need for prolonged reaction times, and the requirement for expensive equipment.
Modern Synthesis of EBCH
Modern synthesis of EBCH involves the use of more advanced techniques, such as enzymatic reduction, microwave-assisted reduction, and flow chemistry.
One of the most popular methods of modern synthesis of EBCH is the enzymatic reduction of 6-bromo-2-oxo-1,2-oxazolidin-3-one using Candida antarctica lipase B (CALB) in the presence of a hydroxy acid, such as citric acid or tartaric acid.
The resulting 6-(tert-butyl)-2-oxo-1,2-oxazolidin-3-one can then be treated with sodium bis(2-hydroxyethyl) sulfite to produce EBCH.
The modern synthesis of EBCH has several advantages, such as the use of environmentally friendly reagents, the high yield and selectivity of the reaction, and the short reaction times.
However, this method also has several disadvantages, such as the high cost of enzymes and the need for specialized equipment.
Biotechnological Synthesis of EBCH
Biotechnological synthesis of EBCH involves the use of biological systems, such as microorganisms, yeast, or enzymes, to produce the desired product.
One of the most promising methods of biotechnological synthesis of EBCH is the use of microorganisms, such as Escherichia coli, to produce 6-bromo-2-oxo-1,2-oxazolidin-3-one.
The resulting 6-bromo-2-oxo-1,2-oxazolidin-3-one can then be treated with sodium bis(2-hydroxyethyl) sulfite to produce EBCH.
The biotechnological synthesis of EBCH has several advantages, such as the low cost of production, the high yield and selectivity of the reaction, and the ease of scaling up the reaction.
However, this method also has several disadvantages, such as the need for specialized equipment and the potential for contamination.
Conclusion
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