Sodium Bicarbonate → HCID 90370153, compound

Participants

Reaction Steps

To a mixture of 1.00 g of methyl 4-{2-[4-({[2-({3-[(pentan-3-ylamino)methyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate, 1.00 g of sodium triacetoxyborohydride, 0.50 mL of acetic acid and 20 mL of methylene chloride was added 473 mg of ethyl 4-[methyl(2-oxoethyl)amino]-4-oxobutanoate, followed by stirring for 1 hour at room temperature. 498 mg of sodium triacetoxyborohydride and 237 mg of ethyl 4-[methyl(2-oxoethyl)amino]-4-oxobutanoate were further added to the reaction mixture, followed by stirring for 2 hours at room temperature. An aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate), thereby obtaining 1.19 g of methyl 4-(2-{4-[({2-[(3-{[{2-[(4-ethoxy-4-oxobutanoyl)(methyl)amino]ethyl}(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate.

Provenance & Evidence