Abstract: Carbon and nitrogen are ubiquitous elements in drugs and drug candidates. The formation of carbon-nitrogen bonds is central to the synthesis of these active pharmaceutical ingredients. This talk will focus on two unique examples of C-N bond-forming reactions we have used at Merck. In elbasvir/ruzasvir, we will highlight a novel dynamic asymmetric Pd-catalyzed C-N coupling, and in letermovir, an organocatalyzed intramolecular asymmetric conjugate addition of a guanidine moiety onto an α,β-unsaturated ester.
Bio: Dr. Rebecca T. Ruck earned her A.B. summa cum laude from Princeton University in 1998 before moving on to Harvard as an NSF fellow in the lab of Prof. Eric Jacobsen. She continued her career as an NIH post-doctoral fellow at UC-Berkeley in the lab of Prof. Robert Bergman. She moved on to Merck Process Research & Development in 2005, steadily assuming roles of increasing amounts of responsibility in the intervening years. She has managed a Discovery Process Chemistry team at the interface of medicinal and process chemistry, served as Director of Catalysis and Automation, which also involves managing efforts around reaction mechanism and flow chemistry, and is currently Director of Process Chemistry. She has made contributions to programs related to Hepatitis C, diabetes and antibacterials, among others. For her role in the chemistry of the beta-lactamase inhibitor, MK-7655, she was recognized as an ACS Division of Organic Chemistry Young Investigator in 2014 and for her commitment to both scientific excellence and advancing women in chemistry, was recognized as one of the ACS Women’s Chemist Committee 2016 Rising Stars. During her time at Merck, Rebecca has played a significant role in Merck’s commitment to safety and is highly active in a variety of external reputation activities, including serving as the departmental recruiting lead, running a series of Merck-sponsored academic lectureships and coordinating the WCC-Merck Research Award for 3rd/4th year female graduate students and accompanying symposium. Becky was recently named the 2018 winner of the ACS Award for Encouraging Women into Careers in the Chemical Sciences.