Bifunctional molecules with antibody-recruiting and entry inhibitory activity against the human immunodeficiency virus

A method of synthesizing a compound according to the chemical structure 16:

• where n and n′ are each independently an integer from 1 to 6, or a pharmaceutically acceptable salt thereof,
• comprising reacting compound 10
• with compound 4
• in the presence of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4 in dimethylformamide/water to produce compound 11 according to the chemical structure:
• which is then reacted with N-(9-Fluorenylmethoxycarbonyloxy)succinimide (Fmoc-OSU) to produce compound 12
• where Fmoc is a fluorenylmethoxycarbonyloxy group and Boc is a tertiarybuyloxycarbonyl group;
• Compound 12 is then deprotected with trifluoroacetic acid to remove the Boc group to produce compound 13
• or its triflouoroacetate salt, which is reacted with compound 2
• to produce compound 14
• which is deprotected to remove the Fmoc group to produce compound 15
• compound 15 is then reacted with alkyne compound 8
• where DNP is a dinitrophenyl group, in the presence of copper sulfate (CuSO4) and ascorbate to produce compound 16 or a pharmaceutically acceptable salt thereof.