Tetrahedron

Efficient kg-scale synthesis of thrombin inhibitor CRC 220

J Heiner, S Bernhard, H Joerg, K Bernd, W Joachim…

文献索引：Jendralla, Heiner; Seuring, Bernhard; Herchen, Joerg; Kulitzscher, Bernd; Wunner, Joachim; et al. Tetrahedron, 1995 , vol. 51, # 44 p. 12047 - 12068

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被引用次数: 33

摘要

Potent thrombin inhibitor 2 is prepared in 10 steps with 20% overall yield from commercial 4 on a kg-scale by the convergent approach depicted in Schemes 1 and 2. The (R)- configuration of the 4-amidinophenylalanine piperidide moiety is controlled by asymmetric hydrogenation. A novel method, the hydrogenolysis of amidoximes 11 and 21, is employed to attain a particularly clean transformation of the cyano into the amidinium functionality. ...