Organic Process Research and Development p. 270 - 283 (2015)
Update date:2022-08-16
Topics:
Littler, Benjamin J.
Aizenberg, Michael
Ambhaikar, Narendra B.
Blythe, Todd A.
Curran, Timothy T.
Dvornikovs, Vadims
Jung, Young C.
Jurkauskas, Valdas
Lee, Elaine C.
Looker, Adam R.
Luong, Hoa
Martinot, Theodore A.
Miller, David B.
Neubert-Langille, Bobbianna J.
Otten, Pieter A.
Rose, Peter J.
Ruggiero, Piero L.
The scale-up of a prototype HCV protease inhibitor (1) from gram scale in the laboratory to kilogram scale in the pilot plant is described. Key features of the optimization included the synthesis of bulk quantities of exomethylene proline intermediate 6, separation of the diastereomers of spirocycle 2 without chromatography, isolation of the precursor to 1 to purge byproducts that might raise genotoxic structural alerts, and purification of an amorphous drug substance via a crystalline acetic acid solvate.
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(2015)