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

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%). Telaprevir has been developed via the novel synthesis of β‐amino‐α‐hydroxy amide and tripeptide acid. The synthesis of β‐amino‐α‐hydroxy amide was designed via the monochloro intermediate using the crossed Claisen condensation followed by decarboxylation with good overall yield and the tripeptide acid was developed by the coupling of dipeptide acid with bicyclic nitrile followed by simple chemical conversions with good overall yield.