Triethylamine → HCID 10950276, compound

Participants

Reaction Steps

To a solution of N-benzyloxycarbonyl-L-valine (460 mg) and diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (500 mg) in dimethylformamide (50 ml) were added diethyl cyanophosophonate (298 mg) and triethylamine (0.191 ml) and the whole was stirred at room temperature for 15 hours. Aftert concentration under reduced pressure, to the residue was added 0.1N hydrochloric acid (50 ml) and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively and dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was dissolved in methanol (20 ml) and stirred at room temperature with 10% palladium on activated carbon (150 mg) under hydrogen atmosphere for 1 hour. After filtration, the filtrate was concentrated under reduced pressure to give a residue, which was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to afford the title compound (663 mg).

Provenance & Evidence