Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 20, Issue 5, Pages 965-969Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.6b00063
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A scalable, asymmetric route for the synthesis of the influenza virus replication inhibitor 2 is presented. The key steps include an enzymatic desymmetrization of cis-1,3-cyclohexanediester in 99% yield and 96% ee, SNAr displacement of a methanesulfinylpyrimidine, and a Curtius rearrangement to form a morpholinyl urea. This high-yielding route allowed us to rapidly synthesize hundreds of grams of 2 in 99% purity to support in vivo studies.
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