Guanidine Hydrochloride → HCID 178505333, compound

Participants

Reaction Steps

Guanidine hydrochloride (6.23 g, 65.2 mmol) was added to a mixture of sodium methoxide (3.52 g, 65.2 mmol) and N,N-dimethylformamide (25 ml), and the resulting mixture was stirred at room temperature for 1 hour. The solid precipitated was filtered off and a solution of (2-ethoxycarbonyl-1-methyl-1H-indol-6-yl) 2,3,4-tri-O-acetyl-β-D-glucopyranosideuronic acid (1.70 g, 3.26 mmol) in N,N-dimethylformamide (9 ml) was added to the filtrate obtained, followed by stirring at room temperature for 7 hours. After toluene was added to the reaction mixture, the resulting mixture was concentrated under reduced pressure, and the resulting residue was purified by a reversed phase column chromatography (eluent; water:methanol=9:1) to obtain a free compound. The free compound was dissolved in water (50 ml) and methanesulfonic acid (1.15 g) was added thereto under ice-cooling. Subsequently, the solvent was distilled off under reduced pressure and the resulting residue was washed with tetrahydrofuran to obtain 0.78 g of [2-[[[amino(imino)methyl]amino]carbonyl]-1-methyl-1H-indol-6-yl] β-D-glucopyranosideuronic acid methanesulfonate.

Provenance & Evidence