Dicyclohexylcarbodiimide → HCID 54763972, compound

Participants

Reaction Steps

A mixture of 2-(2-acetylthiophen-3-ylamino)-2-phenylacetic acid (I4) (188 mg, 0.68 mmol), (R)-quinuclidin-3-ol (104 mg, 0.82 mmol), HOBT (125 mg, 0.82 mmol) and DCC (169 mg, 0.82 mmol) in dry THF (8 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by preparative HPLC. The fractions containing the product were combined and evaporated under vacuum. The residue was dissolved in 2M K2CO3 and extracted twice with EtOAc to obtain (2-acetyl-thiophen-3-ylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (48 mg, 18% yield).

Provenance & Evidence