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Practical Synthesis of a Cathepsin S Inhibitor: Route Identification, Purification Strategies, and Serendipitous Discovery of a Crystalline Salt Form

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posted on 2010-03-19, 00:00 authored by Xiaohu Deng, Jimmy T. Liang, Matthew Peterson, Raymond Rynberg, Eugene Cheung, Neelakandha S. Mani
A “redox economical” strategy resulted in a concise, modular synthesis of compound 1, a potent Cathepsin S inhibitor. Starting from three building blocks, crude drug substance was prepared in a two-step sequence in high yield. Efficient purification of the crude drug substance was accomplished via the formation of an unusual monoethyl oxalate salt.

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