Triethylamine → HCID 67605946, compound

Participants

Reaction Steps

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (500 mg, 1.50 mmol) in THF (15 ml) and DCM (5 ml), was added triethylamine (591 μl, 4.25 mmol), and the reaction was stirred at RT for 10 minutes. Then DCC (309 mg, 1.50 mmol), HOBT (203 mg, 1.50 mmol), and 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (314 mg, 1.25 mmol) were added, and the reaction was stirred at RT for 15 hours. The solvent was evaporated, the residue was taken up with DCM, and the insoluble was removed by filtration. The organic solution was washed twice with 1N Na2CO3 and brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5) to obtain (R)-quinuclidin-3-yl 2-(2-(tert-butoxycarbonylamino)-2-phenylacetamido)-2-phenylacetate (210 mg, 34% yield).

Provenance & Evidence