Solid-Phase Acylating Agents: Immobilized 1-Hydroxybenzotriazole-6-carboxylic Acid

Aurora has developed a line of novel functionalized solid phase acylating reagents. Si-HOBt (Catalog # H 1002, 1-hydroxybenzotriazole-6-carboxamidopropyl silica gel) and Cellulose-HOBt (Catalog # H 1002-DSK-05, 1-hydroxybenzotriazole-6-carboxylate cellulose ester) are utilized for the formation of immobilized activated ester and sulfonate ester reagents for the facile formation of amides and sulfonamides, respectively. The immobilized HOBt is activated utilizing standard coupling chemistry with carboxylic acids (or sulfonyl chlorides) followed by reaction with amines to generate high yields of pure amide and sulfonamide products after filtration. Immobilized HOBt is quite suitable for combinatorial synthesis applications.  Si-HOBt and Cellulose-HOBt offer distinct advantages over polystyrene reagents and other silica gel bound acylating agents. 

Why Si-HOBt and Cellulose-HOBt reagents? 

Si-HOBt and Cellulose-HOBt offer distinct advantages over polystyrene reagents and other silica gel bound acylating agents:

1) Recyclable: Used Si-HOBt is readily regenerated for further use. 

2) Solvent Independent: Works with a wide variety of solvents, including aqueous mixtures, without shrinking or swelling. 

3) Ease of Use: Can be used in a flow-through capacity or agitated by shaking. Furthermore, Si-HOBt is also amenable to overhead stirring and even using magnetic stirrers for up to four hours. 

4) Reproducibility and Scalability: Reactions perform the same on small and large-scale applications. What works in the lab will work in production.

5) Green Chemistry: The ability to easily minimize solvent use results in less waste generated. Compatible with “green solvents” such as 2-methyltetrahydrofuran, ethyl acetate and ethanol.

Educational applications may be found here. Immobilized HOBt products can be found in our shop.