Hydrochloric Acid → HCID 178450553, compound

Participants

Reaction Steps

To a suspension of {(R)-[4-(2-tert-butoxy-ethoxy)-phenyl]-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (260 mg, 0.36 mmol) in 6:1 v/v acetonitrile/p-dioxane (14 mL) at 0° C. under an atmosphere of nitrogen was added 4.0 M hydrogen chloride in p-dioxane (420 μL, 1.68 mmol) and the resulting solution stirred at room temperature for 1 hour. Additional 4.0 M hydrogen chloride (420 μL, 1.68 mmol) was added and stirring continued for 30 minutes. The solvent was removed in vacuo and the residue was basified with saturated aqueous sodium hydrogen carbonate solution. The aqueous mixture was extracted with ethyl acetate (2×25 mL), washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (R)-2-amino-2-[4-(2-tert-butoxy-ethoxy)-phenyl]-N-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-acetamide which was used in the subsequent step without further purification (210 mg, 94%).

Provenance & Evidence