Diazetidine By-Product Formation With DCC + HOBt Mechanism | Organic Chemistry
The mechanism for the formation of a diazetidine by-product that is produced in the DCC peptide coupling reaction where HOBt is included as an additive. In order to reduce the epimerization level when using carbodiimides as coupling reagent, it has been shown that when 1-hydroxy-1H-benzotriazole (HOBt) was included as an additive, yields increased and epimerization levels decreased. However, when using these two reagents together, this side reaction can occur yielding the diazetidine by-product.
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