HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide | HCID 46938715 | — |
| Reactant | 10-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-amine | HCID 68931234 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | Ammonia | HCID 222 | — |
| Product | 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 | HCID 86616474 | — |
Reaction Steps
10-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-amine (Preparation 3, 170 mg, 0.33 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 180 mg, 0.33 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) for 12 hours. Ethyl acetate (20 ml) and water (10 ml) were added and the organics separated, washed with water (10 ml), dried (magnesium sulphate) and the solvent removed in vacuo. 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, 90 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07612084B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-198d5fd5251843668dfc186333ba0bbf |
| Source note | uspto-grants-2009_11 |