HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → 5-[(R)-2-{(R)-2-[3-(2-Aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | [2-(3-{(R)-2-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)ethyl]carbamic Acid tert-Butyl Ester | HCID 66781587 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | 5-[(R)-2-{(R)-2-[3-(2-Aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one | HCID 66781511 | — |
Reaction Steps
A solution of [2-(3-{(R)-2-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)ethyl]carbamic acid tert-butyl ester (2.8 g) in 20% trifluoroacetic acid in DCM was stirred at room temperature for 3 h. Saturated aqueous sodium bicarbonate solution was added to neutralize the TFA and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394275B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-499fa0fd3df44d14960475f7ab7132de |
| Source note | uspto-grants-2016_07 |