HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 3-{3-[(7-{[(2R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}heptyl)oxy]propyl}benzenesulfonamide acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 3-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide | HCID 69316214 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 3-{3-[(7-{[(2R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}heptyl)oxy]propyl}benzenesulfonamide acetate | HCID 69322285 | — |
Reaction Steps
A solution of 3-(3-{[7-(benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide (36 mg) in ethanol (10 ml) with ethyl acetate (2 ml) and glacial acetic acid (1 ml) was hydrogenated using 10% palladium on carbon (50% water by weight, 10 mg) and 20% palladium hydroxide on carbon (10 mg) for 19 h. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified on an aminopropyl SPE cartridge (2 g), eluting with methanol-dichloromethane mixtures. Evaporation of the appropriate fractions with glacial acetic acid gave the title compound (15 mg). LCMS RT=2.26 min ES+ve m/z 532 (MH)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07402598B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-f8b9915ba1a046f2ace7df6af5b37163 |
| Source note | uspto-grants-2008_07 |