Journal
INTERNATIONAL JOURNAL OF PHARMACEUTICS
Volume 611, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.ijpharm.2021.121324
Keywords
Process analytical technology; PAT; Ketal deprotection; Reaction monitoring; In situ analysis; Vibrational spectroscopy
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Funding
- Merck Sharp Dohme Corp.
- MRL Postdoctoral Research Fellowship Program
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The study investigates the real-time monitoring of ketal deprotection reaction using process analytical technology tools, showing that characteristic bands can be used to track the changes in reactants and products. This approach provides valuable insights for understanding and optimizing pharmaceutically-relevant deprotection processes in the future.
The use of protection groups to shield a functional group during a synthesis is employed throughout many reactions and organic syntheses. The role of a protection group can be vital to the success of a reaction, as well as increase reaction yield and selectivity. Although much work has been done to investigate the addition of a protection group, the removal of the protection group is just as important - however, there is a lack of methods employed within the literature for monitoring the removal of a protection group in real time. In this work, the process of removing, or deprotecting, a ketal protecting group is investigated. Process analytical technology tools are incorporated for in situ analysis of the deprotection reaction of a small molecule model compound. Specifically, Raman spectroscopy and Fourier transform infrared spectroscopy show that characteristic bands can be used to track the decrease of the reactant and the increase of the expected products over time. To the best of our knowledge, this is the first report of process analytical technology being used to monitor a ketal deprotection reaction in real time. This information can be capitalized on in the future for understanding and optimizing pharmaceutically-relevant deprotection processes and downstream reactions.
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