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1. Kilogram Scale Synthesis of the Pyrazinone Acetic Acid Core of an Orally Efficacious Thrombin Inhibitor

Author

Nan Zheng, Ralph P. Volante, Terry A. Lyle, Fred J. Fleitz, and Joseph D. Armstrong

Subjects
Reaction conditions, Chemistry, Organic Chemistry, chemistry.chemical_element, Key features, Combinatorial chemistry, Ruthenium, Catalysis, Acetic acid, chemistry.chemical_compound, Thrombin, Reagent, medicine, Organic chemistry, medicine.drug
Abstract

A multi-kilogram scale synthesis of the orally efficacious thrombin inhibitor 1 has been achieved via construction of the pyrazinone core from an unsymmetric oxalic diamide. Key features include judicious choice of reagents to minimize side products, a key ruthenium catalyzed oxidation, and development of reaction conditions amenable to large-scale synthesis.

Published
2000
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