Polymere aminoschutzgruppen auf basis von tert‐butoxycarbonyl‐ und benzyloxycarbonylfunktionen enthaltenden polymethacrylamiden

Abstract

AbstractThe synthesis of tert‐butoxycarbonyl‐ and benzyloxycarbonyl‐modified monomers was performed by the addition of p‐chlorophenyl isocyanate or benzyl isocyanate to the free OH groups of N‐(2‐hydroxy‐2‐methylpropyl)methacrylamide (1), N‐(2‐hydroxy‐2‐methylpropyl)‐6‐methacrylamidohexanamide (2) and N‐β‐hydroxyphenethylmethacrylamide (3). The monomers were homopolymerized and copolymerized with MMA. The kinetics of acidic‐induced amine cleavage from the new amino‐protecting groups was followed by NMR spectroscopy and it became evident that the polymers are suitable amino‐protecting groups. Ca2+ ions enhance the rate of amine cleavage considerably. Neighboring group effects, the influence of comonomers and spacer groups on the reactivity of the urethane groups are also discussed.