op8b00095_si_001.pdf (1.7 MB)
A Convergent Continuous Multistep Process for the Preparation of C4‑Oxime-Substituted Thiazoles
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’SullivanWe
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.
