Dicyclohexylcarbodiimide → ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

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Reaction Steps

A mixture of 2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I64) (951 mg, 2.51 mmol), (R)-quinuclidin-3-ol (694 mg, 5.47 mmol), HOBT (837 mg, 5.47 mmol), and DCC (1.13 g, 5.47 mmol) in dry THF (35 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was partitioned between DCM and 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DMC/MeOH=97/3 to 95/5) to obtain ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (348 mg, 27.5% yield).

Provenance & Evidence