Dicyclohexylcarbodiimide → HCID 67124909, compound

Participants

Reaction Steps

2-(Benzo[b]thiophen-3-yl)-2-(3-(ethoxycarbonyl)phenylamino)acetic acid (I49) (998 mg, 2.81 mmol), HOBT (430 mg, 2.81 mmol), and DCC (1159 mg, 5.62 mmol) were dissolved in THF (28 ml). The mixture was stirred at r.t. for 30 minutes, and then (R)-quinuclidin-3-ol (714 mg, 5.62 mmol) was added. The resulting reaction mixture was stirred at r.t. overnight. The solvent was evaporated, and the crude product was partitioned between EtOAc and sat. Na2CO3. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH=95/5) to collect ethyl 3-(1-(benzo[b]thiophen-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (222 mg, 17.0% yield over two steps).

Provenance & Evidence