Dimethylformamide → HCID 23302093, compound

Participants

Reaction Steps

Combine 1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (3.5 g, 0.0053 mol), prepared as in step C or example 1, with potassium t-butoxide (2.7 g, 0.024 mol) and 1-iodobutane (2.57 mL, 0.024 mol) in dimethylformamide (10 mL). Stir the reaction for 18 hours. Concentrate the reaction under vacuum (0.5 mm at 45° C.) and dissolve the residue in ethyl acetate (500 mL). Wash with water (2×100 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (20% ethyl acetate/hexane, silica gel) to provide 1,18-bis-(butyl)-1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (1.32 g), Rf =0.36 eluting with 20% ethyl acetate/hexane.

Provenance & Evidence