Lithium Hydroxide → (S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid

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Reaction Steps

To a solution of (S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid ethyl ester (4.2 g, 9.8 mmol) in 1,4-dioxane (100 mL) and water (10 mL) was added LiOH (234 mg, 9.8 mmol) at room temperature. The solution was stirred at the same temperature for 12 hours. The solution was concentrated and water was added to the residue. The solution was acidified by 12N HCl in an ice-bath. The solid that precipitated out from the solution was collected by filtration. The solid was dried under vacuum and was confirmed to be the desirable product (S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid (3.7 g, 92%). LC-MS (M++1): 406.27.

Provenance & Evidence