Ammonium formate → Ammonium formate

Participants

Reaction Steps

Palladium hydroxide (10% on carbon, 20 mg) was added to a stirred solution of ammonium formate (344 mg, 5.46 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-{[10-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-yl]amino}-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Preparation 4, 90 mg, 0.091 mmol) in methanol (10 ml) at room temperature. The reaction was heated under reflux for 1 hour, cooled to room temperature and filtered through Arbocel™. The filtrate was collected and the solvent removed in vacuo to yield N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(10-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}decyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide as a mixture with residual ammonium formate. LRMS: m/z 811 [M+H]+. This mixture was dissolved in tetrahydrofuran (4 ml) and methanol (2 ml) and triethylaminetrihydrofluoride (88 ul, 0.54 mmol) was added in one portion at room temperature. The reaction was stirred for 12 hours and the solvent removed under reduced pressure, the residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a glass, 35 mg.

Provenance & Evidence