Medicinal chemistry is an integrated discipline that primarily concerns the design, discovery, synthesis, identification, and interpretation of biologically active compounds at the molecular level. To assist undergraduates in understanding the core subjects of medicinal chemistry, we introduced a closed-loop education mode combining fundamentals of theoretical and experimental aspects in an undergraduate medicinal chemistry experimental course. Since the "Antibiotics" chapter is an important component in our medicinal chemistry lecture course, the topic "design, synthesis and biological evaluation of [beta]-lactamase inhibitors" was selected to train the students' experimental skills and especially the ability to expand on their acquired learning. The whole course schemes, including course introduction, molecular design, chemical synthesis, biochemical testing, docking simulation, student presentation, and academic writing, were described. The [beta]-lactamase inhibitory activities of synthesized benzoxaborole compounds were discussed on the basis of experimental and computational results. The education experiences regarding course process assessment, teaching management, and student self-evaluation were also summarized. These practices will be useful to solidify medicinal chemistry knowledge, train experimental skills, and improve scientific research ability for undergraduates.