Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors

A practical and efficient route toward synthesis of amino acid derivatives containing β-quaternary center has been developed using diastereoselective Strecker reaction. The method was employed for preparation of >100 g of β-methylcyclohexyl glycine derivative, 21. Incorporation of some of the hindered amino acid derivatives at the P3 position resulted in potent HCV NS3 serine protease inhibitors.

Graphical abstractA practical and efficient route toward synthesis of amino acid derivatives containing β-quaternary center has been developed using diastereoselective Strecker reaction. The method was employed for preparation of >100 g of β-methylcyclohexyl glycine derivative, 21. Incorporation of some of the hindered amino acid derivatives at the P3 position resulted in potent HCV NS3 serine protease inhibitors.Download full-size image