Synthesis of a new azapeptide with renin‐inhibiting properties

Abstract

Abstract Boc‐hydrazine ( 1 ) was treated with 4‐nitrophenyl chloroformate ( 2 ) to give Boc‐Azagly 4‐nitrophenyl ester ( 3 ). Reaction of 3 with H‐ACHP‐Ile‐3‐pyridylmethylamide 5) ( 4 ) provided Boc‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide ( 5 ). This was deprotected with HCl/dioxane to give H‐Azagly‐ACHP‐Ile‐3‐pyridylmethylamide dihydrochloride ( 6 ), which was coupled with Boc‐Phe‐OH ( 7 ) by the carbodiimide/HOBt method providing the final azapeptide Boc‐Phe‐Azagly‐ACHP‐3‐pyridyl‐methylamide ( 8 ). This compound was shown to be a renin inhibitor of high specificity.