Kilogram scale synthesis of the pyrazinone acetic acid core of an orally efficacious thrombin inhibitor

FJ Fleitz, TA Lyle, N Zheng, JD Armstrong III…

Index: Fleitz, Fred J.; Lyle, Terry A.; Zheng, Nan; Armstrong III, Joseph D.; Volante Synthetic Communications, 2000 , vol. 30, # 17 p. 3171 - 3180

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Citation Number: 18

Abstract

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.