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New and Efficient Synthesis of HCV NS3/4 A Protease Inhibitor Telaprevir
Author(s) -
Porala Subbanarasimhulu,
Yerrabelly Jayaprakash Rao,
Kasireddy Venkateshwar Reddy,
Yerrabelly Hemasri,
Ghojala Venkat Reddy,
Rebelli Pradeep
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902078
Subject(s) - telaprevir , tripeptide , ns3 , chemistry , yield (engineering) , stereochemistry , amide , dipeptide , nitrile , amino acid , decarboxylation , protease , protease inhibitor (pharmacology) , hepatitis c virus , organic chemistry , biochemistry , virology , biology , virus , enzyme , materials science , ribavirin , antiretroviral therapy , viral load , metallurgy , catalysis
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 β‐amino‐α‐hydroxy amide 2 and tripeptide acid 3 . The synthesis of β‐amino‐α‐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%).
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