Hydrochloric Acid → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid

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Reaction Steps

Lithium hydroxide monohydrate (7.2 mg, 0.17 mmol) is dissolved in water (1.0 mL) and it is added into the solution of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl ester (25 mg, 0.057 mmol) in methanol (1.0 mL) at room temperature. The mixture is stirred for 2 hr and then 1.0 M HCl solution (0.5 mL) is added along with water (10 mL). The mixture is extracted with EtOAc (3×10 mL) and the organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by preparative TLC using 5% MeOH in CH2Cl2 with 1% acetic acid afforded 21 mg (87%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid. LCMS (ESMS): m/z 425.22 (M+H+).

Provenance & Evidence