… ) acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy (4-phenylbutyl) phosphinyl] oxy]-1-oxohexyl]-L-proline, …

DS Karanewsky, MC Badia, DW Cushman…

Index: Karanewsky; Badia; Cushman; DeForrest; Dejneka; Loots; Perri; Petrillo Jr.; Powell Journal of Medicinal Chemistry, 1988 , vol. 31, # 1 p. 204 - 212

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Citation Number: 99

Abstract

(DCC)/(N, N-dimethy1amino) pyridine (DMAP) mediated coupling of phosphonous acids 6a- 0 with (hydroxyacyl)-prolines 3b-g and oxidation of the resulting phosphonous monoesters to phosphonic monoesters 7a-t with sodium metaperiodate in aqueous dioxane. This method has proven to be very general and can be used to prepare phosphonic monoesters of even tertiary alcohols with phosphonous acids of a wide variety of structural types. 4 ...