HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic acid → 6-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic acid | HCID 62406 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Chloro-4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester | HCID 54688537 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-Chloro-1-(4-methoxy-benzyl)-2-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester | HCID 21020252 | 90.2% |
Reaction Steps
A solution of 10 (63.0 mg, 0.16 mmol), DMAP (7.0 mg, 0.054 mmol), and diisopropylethylamine (19.0 mg, 0.15 mmol) in anhydrous CH2Cl2 was treated with trifluoromethylsulfonic acid (78.0 mg, 0.28 mmol). The reaction was stirred at room temperature for 30 min and concentrated. Chromatography (SiO2, 3:1 Hex/EtOAc) gave 11 (75.0 mg, 88%) as a amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07019141B2 |
| Source dataset | uspto-grants-2006_03 |
| ORD ID | ord-1d1b24fbbea04195bd65c159a1997ac5 |
| Source note | uspto-grants-2006_03 |