N-[1-(Benzotriazol-1-yl)alkyl]amides from N-acyl-a-amino acids or N-alkylamides

摘要

A variety of N-(1-methoxyalkyl)amides react with benzotriazole in the presence of PPh_3?HBF_4 and organic bases (Hünig’s base, DBU or DABCO) or solid-state-supported bases (SiO_2-Pip or IRA-67) in CHCl_3 to give N-[1-(benzotriazol-1-yl)alkyl]amides in good yields. The most convenient and efficient procedure for obtaining N-[1-(benzotriazol-1-yl)alkyl]amides consists, however, of the addition of benzotriazole sodium salt to a solution of crude 1-(N-acylamino)alkyltriphenylphosphonium salt, obtained in situ from N-(1-methoxyalkyl)amides and PPh_3?HBF_4. A combination of these reactions with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids in the presence of SiO_2-Pip enables an effective two-pot transformation of N-acyl-α-amino acids to N-[1-(benzotriazol-1-yl)alkyl] amides.