80828-33-7

Upstream product

• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid tert-butyl ester 
• 84793-24-8 N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride 
• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid 1,1-dimethylethyl ester 
• 80828-13-3 (+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 3770-50-1 2-carbethoxyindole 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 84324-12-9 N-<1(R)-(ethoxycarbonyl)-3-phenylpropyl>-(S)-alanine 
• 108507-43-3 (2R,3aR,7aR)-Octahydro-indole-2-carboxylic acid tert-butyl ester 

Downstream Products

• 80828-34-8 Indolapril diacid 
• 80828-32-6 Indolapril hydrochloride 
• 108449-51-0 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Carboxy-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 
• 108449-50-9 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 
• 108449-53-2 (2R,3aR,7aR)-1-[(S)-2-((R)-1-Carboxy-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 
• 108449-52-1 (2R,3aR,7aR)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid; hydrochloride 

Relevant academic research and scientific papers

Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives

A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.