Preparation of aminoalkylmaleimides and their conjugates with haptens and antigens

Abstract

Title compds. (I; R1, R2 = H, alkyl; A = C2-6 alkylene) and II (X = hapten or antigen), were prepd. Thus, H2NCH2CH2NHCO2CMe3 in aq. NaHCO3 at 0 Deg was treated with N-(ethoxycarbonyl)maleimide and the mixt. was stirred at room temp. with addn. of THF to give 92% N-(tert-butoxycarbonyl)-2-(N-maleimido)ethylamine, which was treated with aq. HCl in dioxane to give 2-(N-maleimido)ethylamine.HCl. This was condensed with a variety of haptencarboxylic acid N-hydroxysuccinimide esters (prepn. given) to give, e.g., adduct III. [on SciFinder (R)]