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Thursday, August 27 • 4:00pm - 4:20pm
[0009] Scale Up of Azaindole Compound: A Story of Synthetic Evolution

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Azaindole compound is a potent inhibitor of influenza, and has complex structure which is a challenge for scale up. We use enzymatic desymmetrization of 1,3-bisester-cyclohexane to generate the two chiral centers with high yield (99%) and high ee (99%). The first generation of synthesis employs the displacement of chiral monoBoc-diaminocyclohexane with sulfoxide, followed by urea formation (10 steps); The second generation of synthesis is racemic and need SFC separation (6 steps); The third generation of synthesis employs a Curtius rearrangement of acid to install morpholin urea in one step (7 total steps with 33% overall yield). All steps from last route are high yielding and easy to scale up.

ST Lecturers
avatar for Colin Liang

Colin Liang

Sr Research Scientist, Vertex Pharmaceuticals
Sr Research ScientistVertex Pharmaceuticals

Thursday August 27, 2015 4:00pm - 4:20pm PDT
MCC Theater