An article Development of a Large-Scale Route to Glecaprevir: Synthesis of the Macrocycle via Intramolecular Etherification WOS:000563756800002 published article about HYDROGEN; BROMIDES; OLEFINS; ARYL in [Kallemeyn, Jeffrey M.; Engstrom, Kenneth M.; Pelc, Matthew J.; Lukin, Kirill A.; Morrill, Westin H.; Wei, Haojuan; Towne, Timothy B.; Henle, Jeremy; Nere, Nandkishor K.; Welch, Dennie S.; Shekhar, Shashank; Ravn, Matthew M.; Zhao, Gang; Fickes, Michael G.; Cink, Russell D.] AbbVie Inc, Proc Res & Dev, N Chicago, IL 60064 USA; [Ding, Chen; Vinci, John C.; Marren, James] AbbVie Inc, Analyt Res & Dev, N Chicago, IL 60064 USA in 2020.0, Cited 35.0. Name: Diphenylmethanamine. The Name is Diphenylmethanamine. Through research, I have a further understanding and discovery of 91-00-9
Glecaprevir was identified as a potent hepatitis C virus (HCV) protease inhibitor, and a large-scale synthesis was required to support the late-stage clinical trials and subsequent commercial launch. The large-scale synthetic route to glecaprevir required the development of completely new synthetic approaches to the two key structural features: the 18-membered macrocycle 3 and the difluoromethyl-substituted cyclopropyl amino acid 4. In this first manuscript, we describe the route development for the macrocycle 3; the second manuscript will describe the development of a new synthetic route to the difluoromethyl-substituted cyclopropyl amino acid 4 and the final assembly of glecaprevir. The large-scale synthetic route to the macrocycle employed a unique intramolecular etherification reaction as the key step in the macrocycle synthesis, avoiding the scalability limitations of the ring-closing metathesis (RCM) reaction of the enabling route. The large-scale synthetic route to the macrocycle was successfully used to produce the amount of glecaprevir required to support the late-stage clinical development.
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