Design and synthesis of a cocaine-diamide hapten for vaccine development

Article abstract of DOI:10.1016/0040-4039(96)01170-7

A cocaine-diamide hapten was designed in an effort to obtain a potent, long-lasting anti-cocaine immune response for the treatment of cocaine abuse. The analogue incorporated an amido linker functionality in place of the carbomethoxy group at C-2 and a benzoylamino replacement of the benzoyloxy group at C-3 of the cocaine framework. Compound 3 was synthesized in 6 chemical steps starting from (+)-2-carbomethoxy-3-tropinone.