A Practical Transferring Method from Batch to Flow Synthesis of Dipeptides via Acid Chloride Assisted by Simulation of the Reaction Rate
- Masahiro Hosoya
- *Go Shiino
- Naoki Tsuno
- API R&D Laboratory, CMC R&D Division, Shionogi and Co., Ltd., 1-3, Kuise Terajima 2-chome, Amagasaki, Hyogo 660-0813, JapanRead the publication that featured this abstract
This paper proposes a technical approach for seamlessly setting the conditions of continuous flow synthesis from batch data. We directly detected the acid chloride formation from Fmoc-l-Phe-OH in batch using the in-line monitoring technology ReactIR and logically calculated the residence time under continuous flow conditions based on kinetic study. Assisted by this simulation method, the sequential flow operations, which consist of acid chloride formation from Fmoc-l-Phe-OH, cooling and coupling with Fmoc-l-Phe-Cl and H2N-l-Phe-OMe, were completed in approximately 1 min.
Direct detection and quantification of acid chloride was performed by using ReactIR as an in-line monitoring tool. Based on kinetics calculated from the in-line monitoring results, the residence time for acid chloride formation under continuous flow conditions was set. A rapid flow synthesis of a dipeptide via acid chloride was guided by optimized batch conditions.
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