Hydrochloric Acid → {[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-2-methyl-biphenyl-4-ylamino]-methyl}-phosphonic acid

Participants

Reaction Steps

To a solution of ({3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-2-methyl-biphenyl-4-yl amino}-methyl) phosphonic acid diethyl ester (38 mg, 0.057 mmol) in DCM (1.2 mL) at 0° C. was added iodotrimethylsilane (25 μL) over 3 minutes period. After 1 h at 0° C., H2O was added. The mixture was stirred for 30 minutes, and then concentrated to give a brown solid. The solid was dissolved in MeOH (1.32 mL), 20% HCl was added, and stirred at ambient temperature for 3 h. The mixture was concentrated to give a brown solid. To this solid was added TFA/DCM (1:1, 3 mL) and stirred at ambient temperature for 40 minutes. The reaction mixture was then concentrated and purified by HPLC (C18 column, 10–70% CH3CN over 30 minutes) to give the title compound (11 mg, 38% yield) as a white solid.

Provenance & Evidence