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Going Green in Process Chemistry: Optimizing an Asymmetric Oxidation Reaction To Synthesize the Antiulcer Drug Esomeprazole
journal contribution
posted on 2019-10-07, 11:40 authored by Graeme
D. McAllister, Andrew F. ParsonsSustainable practices in process
chemistry are highlighted by a
novel, 9 week team project of 8–12 students, in collaboration
with AstraZeneca chemists, in an organic chemistry laboratory. Students
synthesize the antiulcer medicine esomeprazole, which involves the
asymmetric oxidation of pyrmetazole. To provide insight into the modern
process chemistry industry, they propose environmentally friendly
modifications to the asymmetric oxidation. Students first synthesize
pyrmetazole and then follow a standard oxidation procedure and carry
out modified, greener reactions of their choice. They investigate
how a change in reaction conditions affects both the yield and enantioselectivity
of esomeprazole. Positive student feedback was received and student
postlab reports were analyzed over a 4 year period (2015–2018).
Results consistently showed that the project provided students with
the key tools to develop greener syntheses. This contextual approach
not only offers the opportunity to develop valuable communication
and team-working skills, but it also gives students creative input
into their experimental work. It teaches the important research skills
involved in sustainable process chemistry, from reproducing and modifying
a literature procedure to identifying green metrics.