N,N-Dimethyl-1,3-propanediamine → [11-(3-Dimethylaminopropylcarbamoyl)undecyl]carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 12-tert-butoxycarbonylaminododecanoic acid (3) (205 mg, 0.65 mmol) and 1,1′-Carbonyldiimidazole (114 mg, 0.70 mmol) in anhydrous THF (5 mL) was stirred at room temperature for 3 hours. 3-(Dimethylamino)propylamine (163 mL, 1.30 mmol) was then added via syringe and the reaction mixture stirred at room temperature for a further 24 hours. The solvent was then removed by rotary evaporation and the residue subjected to Biotage silica gel column chromatography (ethyl acetate/dichloromethane 5% to 75%, then methanol/dichloromethane 8%) to give the desired amide 4 (87.0 mg, 34%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.27 (m, 14H), 1.45 (s, 9H), 1.47 (m, 2H), 1.60 (m, 2H), 1.69 (m, 2H), 2.16 (t, 2H), 2.29 (s, 6H), 2.45 (t, 2H), 3.10 (m, 2H), 3.32 (m, 2H), 4.50 (br, 1H), 6.91 (br, 1H). m/z (ESI) 400 [C22H45N3O3+H]+.

Provenance & Evidence