Water → HCID 18920517, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-chloromethylnaphthalene (1.7 g - 9.6 mmol) in 5 ml hexamethylphosphorous triamide (HMPA) is added to a mixture of 1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (2.6 g) and potassium t-butoxide (1.07 gm) in HMPA (50 ml). The mixture is heated in an 80° C. oil bath for 4 hours, poured into 300 ml of water, and the aqeuous mixture is extracted with ethyl acetate (2×300 ml). The combined extracts are extracted with water (3×300 ml) and brine (300 ml). The organic layer is dried, evaporated and the residue is chromatographed (flash-silica gel column eluting with 4 to 1 toluene/ethylacetate to yield 800 mg of 1,18-bis-[(1-naphthyl)methyl]-1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane.

Provenance & Evidence