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The amide bond is the defining molecular structure of proteins and peptides. In addition, a report estimates that as many as 25 % of all synthetic pharmaceutical drugs contain an amide group.1
Therefore, there is an ongoing scientific endeavor to develop efficient amidation methodologies.2
Usually, the amide bond formation relies on the use of an excess of toxic coupling reagents such as carbodiimides or supernucleophiles. These chemicals produce a large amount of by-products, which tends to complicate the isolation and purification of the desired amide product.
The use of a reagent linked to an insoluble material has become a widely used tool since the introduction of the solid-phase synthesis concept.3
Solid-phase reagents are valuable for amide coupling with a carboxylic acid because they generate less unwanted side products.
Other advantages of using solid-supported reagents include improved stability, toxic chemical immobilization, the ability to run multiple transformations in a single pot and the flexibility to use batch reactions, microwave irradiation and flow chemistry.
1 J. Comb. Chem., 1999, 1, 55
2 Tetrahedron, 2005, 61, 10827
3J. Am Chem Soc., 1963, 85, 2149
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SiliaBond® HOBt can be easily activated and should ideally be used with a base such as N,N-diisopropylethylamine in the same condition as in homogeneous solution. Moreover, this supported reagent can be reused a few times without adversely affecting its performance.
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