2-(Dimethylamino)ethanol → Methyl 6-(benzenesulphonylmethyl)-2-(2-dimethylaminoethoxy)-3-(furan-3-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 114, 0.08 g), N,N-dimethylethanolamine (0.024 g) and triphenylphosphine (0.085 g) in dry THF (1 ml) was stirred and cooled to 0° C. A solution of di-isopropyl azodicarboxylate (0.065 g) in dry THF (1 ml) was added dropwise. The resultant mixture was stirred at 0° C. for 10 minutes then at room temperature overnight. Further triphenylphosphine (0.028 g) and di-isopropyl azodicarboxylate (0.022 g) was added and the mixture was stirred at room temperature for 1.5 hours then left to stand at room temperature overnight. The mixture was added to a SCX-2 column and eluted with acetonitrile followed by 2M ammonia in methanol. After evaporation of the basic eluent, the residue was repurified using an SCX-2 column, eluting with methanol followed by 2M ammonia in methanol to give methyl 6-(benzenesulphonylmethyl)-2-(2-dimethylaminoethoxy)-3-(furan-3-yl)benzoate (0.07 g) as a gum.

Provenance & Evidence