Absolute configuration of (-)-4-(3,4-dichlorophenyl)-4-(2-pyridyl)butanoic acid: essential information to determine crucial steric feature of arpromidine-type histamine H_2 receptor agonists

Abstract

The structural information gained from the study of the chiral building block (R)-(-)-4-(3,4-dichlorophenyl)-4-(2-pyridyl)butanoic acid-L-(-)-ephedrine [methyl(1-hydroxy-1-phenylprop-2-yl)ammonium 4-(3,4-dichlorophenyl)-4-(2-pyridyl)butanoate], C10H16NO+·C15H12Cl2NO2-, can be used to deduce the absolute configuration of highly potent arpromidine-type histamine H2 receptor agonists, as the chiral butanoic acid can be converted to (R)-(-)-3-(3,4-dichlorophenyl)-3-(2-pyridyl)propylamine and to the corresponding R-configured arpromidine analogue.