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

Author(s)
Breen, Christopher P.; Jamison, Timothy F
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Abstract
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.
Date issued
2019-10-18
URI
https://hdl.handle.net/1721.1/128240
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Chemistry - A European Journal
Publisher
Wiley-VCH
Citation
Breenand, Christopher P. and Timothy F. Jamison. “Continuous Flow Synthesis of ACE Inhibitors From N-Substituted L-Alanine Derivatives.” Chemistry - A European Journal, 25, 69 (October 2019) © 2019 The Author(s)
ISSN
0947-6539

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