Triethylamine → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-[(1E)-3-[[(2-hydroxy-1,1-dimethylethyl)aminocarbonyl]amino]prop-1-en-1-yl]benzyl]-2-(benzyloxy)-4-methylphenyl)-D-glucitol

Participants

Reaction Conditions

Reaction Steps

To an acetonitrile solution (5.4 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-D-glucitol (0.48 g, 0.539 mmol) were added N-allyl-N′-(2-hydroxy-1,1-dimethylethyl)urea (223 mg, 1.29 mmol), palladium(II) acetate (24 mg, 0.108 mmol), tri-O-tolylphosphine (66 mg, 0.216 mmol) and triethylamine (273 mg, 2.69 mmol), and the mixture was stirred at 120° C. for 20 minutes with microwave manufactured by Biotage. The reaction solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform and then chloroform:methanol=50:1) to obtain the title compound (210 mg, 40%) as a pale yellow amorphous compound.

Provenance & Evidence