Investigation of Halogen-Metal Exchange in the Presence of a β-lactam

Keith Chomsky, Chemistry (on right in photo)

Faculty Mentor: Dr. David Hunt

              Antibiotic compounds such as penicillin contain what is known as a β-lactam ring system.  It is well-known that this ring system is the source of the compound’s biological activity in combating bacteria. The focus of this project is two-fold: 1) to use a halogen-metal exchange reaction to determine if the 4-membered ring can withstand these conditions, and 2) to create derivatives of a bromoaryl-substituted β-lactam system. This reaction will be conducted at significantly low temperatures due to the high reactivity of the β-lactam ring system. The entire procedure consists of the construction of the bromoaryl-substituted β-lactam system followed by the halogen-metal exchange reaction and subsequent electrophilic substitution reaction.

              As seen in the reaction scheme, there is no set electrophile (E+) for this project. During the summer, many electrophiles have been tested for this reaction scheme. Also, a new line of interest in this study is currently under investigation involving 3-bromobenzaldehyde as the starting material. The goal is to study several substitutions in that position in order to possibly create a new line of compounds that can be used in the same way other β-lactam compounds are used today.

Personal Statement

              This program has been a greatly valuable experience for me. Not only have I learned and become confident with many laboratory techniques, but I have gained new friendships that I plan to maintain in the future. Although I have been working by myself on my project, I have learned how to work well with others in a lab area. I was also challenged to think independently and solve problems that arose during the process of the study. Overall, this program has been a huge benefit. I now have this great experience under my belt to take with me to graduate school and beyond.