Dimethylformamide → Pentanediamide

Participants

Reaction Steps

To the above amine was added N-[(N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]glutaramide monocarboxylic acid (0.132 g, 0.256 mmol), EDCI (0.084 g, 0.439 mmol) and 1-hydroxybenzotriazole hydrate [HOBT] (0.030 g, 0.220 mmol) which was then dissolved in DMF (7.5 mL). Dissolution was aided by sonication and the suspension stirred under nitrogen at room temperature for three days with the flask covered with foil. At that time, the DMF was removed via kugelrohr apparatus (0.1 mm Hg, 60° C.). The residue was purified on a silica gel column using a CHCl3 to 7% MeOH/CHCl3 solvent system to give the desired product N-[(N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylpyrrole-2-carboxamido)-2-carboxamido)]-N-[5-(3-benzyloxy-2-(2-chloroethyl)phenyl)benzofuran-2-carboxamido)]glutarodiamide as a tan solid (0.108 g, 52% yield). Rf=0.08 (5% MeOH/CHCl3). M.p. 80-84° C. 1H-NMR (500 MHz, DMSO-d6) 10.21 (s, 1H), 10.04 (s, 1H), 9.82 (s, 1H), 9.81 (s, 1H), 5.09 (s, 3H), 3.82 (s, 3H), 3.78 (s, 3H). FAB-MS (NBA) 949 (M+H+, 1). FAB-MS (NBA+K+) 987 (M+K+, 1). Accurate mass calculated for C50H57N8O9Cl+Na: calcd. 971.3835, obs. 971.3821.

Provenance & Evidence