4-Methoxybenzenesulfonyl chloride → N-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-4-methoxy-benzenesulfonamide

Participants

Reaction Steps

To a solution of 5-aminomethyl-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one bis-hydrochloride (40 mg, 0.092 mmole) in CH2Cl2 (1 mL) and pyridine (1 mL) was added 4-methoxybenzenesulfonyl chloride (0.75 mL, 0.4 M solution in trifluorotoluene, 3 equiv). The reaction was shaken overnight. A polyamine resin was added to quench the excess sulfonyl chloride. The mixture was filtered and concentrated. The residue was dissolved in EtOAc and washed with 1 M NaOH and brine, dried over Na2SO4 and concentrated to give a light brown oil. Purification by chromatography (5% MeOH/CH2Cl2 with 1% NH4OH) gave the title compound as an off-white foam (32 mg, 0.060 mmol, 66%). The structure was confirmed by NMR and mass spectrometry. MS m/z 532 (M++H).

Provenance & Evidence