Methanol → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester

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Reaction Steps

To a solution of 1-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (560 mg, 1.9 mmol) in DMF (9.0 mL) are added methyl acrylate (0.19 mL, 2.1 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.09 mL, 0.19 mmol). The resulting mixture is stirred at room temperature for 3 hr. Then Sat. NH4Cl (5 mL) and water (50 mL) are added and the mixture is extracted with EtOAc (3×50 mL). The organic layers are combined, washed with water (3×75 mL), dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography using 30% EtOAc in hexanes affords 600 mg (83%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester.

Provenance & Evidence