82716-91-4Relevant articles and documents
Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives
Breen, Christopher P.,Jamison, Timothy F.
supporting information, p. 14527 - 14531 (2019/11/03)
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.
Concise, catalytic asymmetric synthesis of tetrahydroisoquinoline- and dihydroisoquinoline-3-carboxylic acid derivatives
Ooi,Takeuchi,Maruoka
, p. 1716 - 1718 (2007/10/03)
Catalytic asymmetric synthesis of tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives 1 has been accomplished by the successful utilization of phase-transfer catalysis of the C2-symmetric chiral quaternary ammonium bromides. Our approach also enables facile synthesis of quaternary isoquinoline derivatives 2 and 3 with high enantiomeric purities.
Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types
Klutchko,Blankley,Fleming,Hinkley,Werner,Nordin,Holmes,Hoefle,Cohen,Essenburg
, p. 1953 - 1961 (2007/10/02)
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