N ‐ tert ‐butoxycarbonyl‐ L ‐leucinal product: N ‐ tert ‐Butoxycarbonyl‐ L ‐leucinal: Boc‐ L ‐leucinal intermediate: Boc‐ L ‐leucine N ‐methyl‐O‐methycarboxamide

The synthesis of a series of novel, potent angiotensin converting enzyme (ACE) inhibitors containing saturated bicyclic amino acids in place of proline is described. Octahydroindole-2-carboxylic acid, octahydroisoindole-1-carboxylic acid, and octahydro-3-oxoisoindole-1-carboxylic acid can replace proline in both sulfhydryl and non-sulfhydryl ACE inhibitors to give compounds equipotent to captopril and enalapril both in vitro and in vivo. Structure-activity relationships are discussed. Compound 11a (CI-907, indolapril) has advanced to clinical evaluation.

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