Methanesulfonyl chloride → methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester

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Reaction Steps

To a solution of 1-[5-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (155 mg, 0.38 mmol) and TEA (130 mg, 1.14 mmol) in DCM (5 mL) was added methanesulfonyl chloride (87 mg, 0.76 mmol) at 0° C. The final solution was stirred at ambient temperature for 12 h then washed with sat. NaHCO3 and brine. The organic layer was dried with MgSO4 and evaporated. The residue was purified by flash chromatography (hexanes:EtOAc 2:1 to 1:1) to give 62 mg (33%) of methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester as a white solid.

Provenance & Evidence