Lithium hydroxide, monohydrate → HCID 59497654, compound

Participants

Reaction Steps

To a stirred solution of 3-[3-(2,3-dimethyl-indolizin-8-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (110 mg, 0.29 mmol) in THF (5 ml) and water (1.5 ml) was added lithium hydroxide monohydrate (25 mg, 0.58 mmol). After 1.5 h the reaction appeared complete (LC-MS) and was subsequently concentrated. The remaining residue was diluted with water (˜12 ml) and acidified to pH˜5 using HOAc (˜5 drops). The resulting solid was dissolved into DCM and the layers were separated. The aqueous phase was extracted with DCM (1×) and the combined organics were concentrated. The remaining green residue was dissolved into a minimal volume of DCM and applied to a preparative TLC plate (1 mm). Eluted with 8% MeOH/DCM. The product-band was isolated and suspended in 5% MeOH/DCM. The silica gel was removed via filtration and washed with DCM. The combined filtrates were concentrated to give the desired product as a light green solid. LCMS (ESMS): m/z 364.24.

Provenance & Evidence