Synthesis of semisynthetic dipeptides using N-carboxyanhydrides and chiral induction on Raney nickel. A method practical for large scale

…, JW Butcher, WE Shearin Jr, J Budavari…

文献索引：Blacklock; Shuman; Butcher; Shearin Jr.; Budavari; Grenda Journal of Organic Chemistry, 1988 , vol. 53, # 4 p. 836 - 844

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被引用次数: 58

摘要

Methods useful for both laboratory and large-scale syntheses of the ACE inhibitors enalapril and lisinopril are described. The requisite dipeptides L-alanyl-L-proline and W- (trifluoroacety1)-L-lysyl-L-proline were prepared via N-carboxyanhydride (NCA) chemistry. These dipeptides undergo facile reductive alkylation with ethyl 2-oxo-4-phenylbutyrate over Raney nickel with high stereoinduction to afford the direct precursors of enalapril maleate ...