American Chemical Society
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A Convergent Continuous Multistep Process for the Preparation of C4‑Oxime-Substituted Thiazoles

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journal contribution
posted on 2018-06-26, 00:00 authored by Edouard Godineau, Claudio Battilocchio, Matthias Lehmann, Steven V. Ley, Ricardo Labes, Letitia Birnoschi, Srinivas Subramanian, C. S. Prasanna, Amol Gorde, Mahesh Kalbagh, Vivek Khade, Anton Scherrer, Anthony C. O’Sullivan
We report a strategy designed for the rapid and convergent assembly of C4-oxime substituted thiazoles. Our approach relied on 3-bromo-2-oxopropanal O-methyl oxime 7 as a key building block. A three-step sequence to 7 was designed, which, for safety concerns, could only be operated in batch mode on limited scales (≪100 g). We describe herein how we addressed such a limitation, by designing a multistep continuous synthesis of this intermediate and further demonstrate the advantages of flow reactor configuration upon scaling up.