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Brown, Maria S; Caporello, Michaella A; Goetz, Adam E; Johnson, Amber M; Jones, Kris N; Knopf, Kevin M; Kulkarni, Samir A; Lee, Taegyo; Li, Bryan; Lu, Cuong V; Magano, Javier; Puchlopek-Dermenci, Angela L. A; Reyes, Giselle P; Ruggeri, Sally Gut; Wei, Lulin; Weisenburger, Gerald A; Wisdom, Richard A; Zhang, Mengtan
Organic process research & development, 06/2021, Letnik: 25, Številka: 6Journal Article
We describe a series of improvements to the synthesis of a 3,8-diazabicyclo3.2.1octane derivative that result in a reduced step count and higher overall efficiency compared to previously published syntheses. Our method includes optimization and mechanistic understanding of a key diastereoselective cyclization to achieve a >95:5 diastereomeric ratio, as well as demonstration of a unique enzyme-catalyzed amidation reaction using hexamethyldisilazane as both an ammonia source and scavenger. Finally, we identify a novel cocrystal solid form of the target compound that provides improved purity and material properties. Demonstration of the new chemistry to prepare >100 kg of the target compound serves to illustrate the robustness of the new process.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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