New and Efficient Synthesis of HCV NS3/4 A Protease Inhibitor Telaprevir

被引：1

作者：

Porala, Subbanarasimhulu ^{[1
,2
,3
]}

Yerrabelly, Jayaprakash Rao ^{[1
]}

Kasireddy, Venkateshwar Reddy ^{[4
]}

Yerrabelly, Hemasri ^{[5
]}

Ghojala, Venkat Reddy ^{[3
]}

Rebelli, Pradeep ^{[3
]}

机构：

[1] Osmania Univ, Univ Coll Sci, Dept Chem, Hyderabad 500004, Telangana, India

[2] Jawaharlal Nehru Technol Univ Coll Engn, Dept Chem, Hyderabad 500085, Telangana, India

[3] MSN R&D Ctr, Dept Res & Dev, Medak 502307, Telangana, India

[4] JNTUH, CMR Engn Coll, Dept Chem, Hyderabad 501401, Telangana, India

[5] Osmania Univ, Dept Chem, Nizam Coll, Hyderabad 500004, Telangana, India

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 33期

关键词：

ss-amino-alpha-hydroxy amide; bicyclic nitrile; crossed Claisen condensation; dichloro intermediate; monochlo intermediate; telaprevir; tripeptide acid; ALPHA-CHLOROKETONES;

D O I：

10.1002/slct.201902078

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and improved approach for the synthesis of HCV NS3/4 A (Hepatitis C virus Non-structural protein 3) protease inhibitor, Telaprevir 1 has been developed, which involves the novel synthesis of key intermediates ss-amino-a-hydroxy amide 2 and tripeptide acid 3. The synthesis of ss-amino-a-hydroxy amide 2 was designed via the monochloro 24, dichloro 25 intermediates using the crossed Claisen condensation followed by decarboxylation with good overall yield (29.62%). The tripeptide acid 3 was developed by the coupling of dipeptide acid 20 with bicyclic nitrile 29 followed by simple chemical conversions in less number of steps with good overall yield (61.2%).

引用

页码：9523 / 9528

页数：6

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