Methanol → Ammonia

Participants

Reaction Steps

N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide (Preparation 61, 250 mg, 0.29 mmol) was dissolved in tetrahydrofuran (10 ml) and methanol (0.5 ml) and triethylaminetrihydrofluoride (1.0 ml, 6.1 mmol) was added. The reaction was stirred for 3 days and the solvent removed in vacuo. The residue was dissolved in 880 ammonia (1 ml) and the solvent removed under reduced pressure, this was repeated 3 times. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 by volume) to furnish the title compound as a pale yellow foam, 100 mg.

Provenance & Evidence