Efficient kg-scale synthesis of Thrombin Inhibitor CRC 220

Autor:	Wunner Joachim, Jendralla Heiner, Kulitzscher Bernd, Herchen Joerg, Seuring Bernhard, Stüber Werner, Koschinsky Rainer
Rok vydání:	1995
Předmět:	Thrombin Chemistry Hydrogenolysis Yield (chemistry) Organic Chemistry Drug Discovery Asymmetric hydrogenation medicine Moiety Biochemistry Combinatorial chemistry medicine.drug
Zdroj:	Tetrahedron. 51:12047-12068
ISSN:	0040-4020
DOI:	10.1016/0040-4020(95)00765-z
Popis:	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. Despite of the amorphous nature of target compound 2, the approach is devoid of any chromatographic purification.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3b67539983eb702b80fe9955ab0dd0c4 https://doi.org/10.1016/0040-4020(95)00765-z Zobrazit plný text záznamu Full Text from ScienceDirect