Dimethylformamide → HCID 54019952, compound

Participants

Reaction Steps

A solution of 3,4-dihydroxycinnamic acid chloride (3) in dimethylformamide at -20° to -15° C. is reacted with 4-O-α-D-glucopyranosyl-β-D-glucopyranosylamine heptaacetate (6) in pyridine at -15° to -5° C. for 30 minutes, then at -5° to +20° C. for 1-2 hours, then extracted with organic solvents, giving N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide, nonaacetate (nonaester) (7). This nonaacetate (7) is then converted to N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide (8) by reaction in methanol, triethylamine and water, under an inert atmosphere at ambient temperature for 20-30 hours followed by refluxing for 2-6 hours and extraction in organic solvents. The free sugar derivative (8) is then reacted with triethylamine sulfur trioxide in N,N-dimethylacetamide under an inert atmosphere at 50°-70° C. for 15-20 hours followed by treatment with an alkali or alkaline earth metal acetate in water giving the products (9), where A is the alkali or alkaline earth metal cation.

Provenance & Evidence