Tributylphosphine → Methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

Tri-n-butylphosphine (0.054 g) was added dropwise to a cooled solution of di-isopropyl azodicarboxylate (0.065 g) in dry THF (1 ml) at 0° C. The resultant solution was warmed to room temperature for 10 minutes then re-cooled to 0° C. A mixture of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 114, 0.05 g) and t-butyl N-(2-hydroxyethyl)-N-methylcarbamate (0.025 g) in THF (1 ml) was added dropwise and the reaction mixture was warmed to room temperature and stirred for 3 hours. Ethyl acetate and water were added and the organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (1:3) to give methyl 6-(benzenesulphonylmethyl)-2-[2-(N-t-butoxycarbonyl-N-methylamino)ethoxy]-3-(furan-3-yl)benzoate (0.054 g) as a gum.

Provenance & Evidence