Hydrochloric Acid → [3-(1-tert-Butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl]-phenethyl-ammonium chloride

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Reaction Steps

tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor J-01b, 199 mg, 0.38 mmol) is dissolved in a 1M HCl solution in ethyl acetate (1.89 ml). The resulting solution is stirred at rt for 1 h. The solvent is evaporated and the crude solid is dissolved in dichloromethane, the resulting organic phase is washed with a saturated aqueous NaHCO3 solution and with water. Evaporation of the solvent in vacuo and chromatography of the residue on silica-gel (dichloromethane/MeOH, 92:8) yields the title compound (107 mg) in 61% as a white solid: tR=2.62 min (LC-2), ESI-MS (pos.): m/z 510.49 [M+H]+.

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