Minimizing HCN in DIC/Oxyma-Mediated Amide Bond-Forming Reactions
Aiming at advancing protocols for safer, environmentally sensible peptide synthesis we report our findings with regard to the occurrence of hydrogen cyanide (HCN, prussic acid) in amide bond-forming reactions mediated by diisopropylcarbodiimide (DIC) and ethyl (hydroxyimino)cyanoacetate (Oxyma).[…]
Aiming at advancing protocols for safer, environmentally sensible peptide synthesis we report our findings with regard to the occurrence of hydrogen cyanide (HCN, prussic acid) in amide bond-forming reactions mediated by diisopropylcarbodiimide (DIC) and ethyl (hydroxyimino)cyanoacetate (Oxyma). We determined that HCN is always formed in amide bond-forming reactions on solid support in N,N-dimethylformamide (DMF) when DIC/Oxyma is employed.
Marion Erny, Marika Lundqvist, Jon H. Rasmussen, Olivier Ludemann-Hombourger, Frédéric Bihel, and Jan Pawlas, Organic Process Research & Development, https://doi.org/10.1021/acs.oprd.0c00227
June 15 2020