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• W2077142848 abstract "A potent reversible inhibitor of the cysteine protease cathepsin-S was prepared on large scale using a convergent synthetic route, free of chromatography and cryogenics. Late-stage peptide coupling of a chiral urea acid fragment with a functionalized aminonitrile was employed to prepare the target, using 2-hydroxypyridine as a robust, nonexplosive replacement for HOBT. The two key intermediates were prepared using a modified Strecker reaction for the aminonitrile and a phosphonation-olefination-rhodium-catalyzed asymmetric hydrogenation sequence for the urea. A palladium-catalyzed vinyl transfer coupled with a Claisen reaction was used to produce the aldehyde required for the side chain. Key scale up issues, safety calorimetry, and optimization of all steps for multikilogram production are discussed." @default.
• W2077142848 created "2016-06-24" @default.
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• W2077142848 date "2010-01-27" @default.
• W2077142848 modified "2023-09-27" @default.
• W2077142848 title "Large-Scale Asymmetric Synthesis of a Cathepsin S Inhibitor" @default.
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• W2077142848 doi "https://doi.org/10.1021/jo9022809" @default.
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