HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-[3-[(4-Chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate | HCID 16073847 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[3-[(4-Chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetic acid | HCID 16073848 | 80.9% |
Reaction Steps
To a suspension of tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-(3-hydroxy-1-propynyl)-4-oxo-1(4H)quinolinyl]acetate (0.07 g) from Example No. 28 in dichloromethane (1 mL) is added trifluoroacetic acid (1 mL). After 3 hours, the resulting solution is concentrated under reduced pressure. The residue is dissolved in a small amount of dichloromethane:methanol:DMF and slowly added to vigorously stirring 1:1 diethyl ether:pentane. The resulting precipitate is collected filtration to afford 0.05 g of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06248739B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-66de466a215248a091e6498e44bd7f50 |
| Source note | uspto-grants-2001_06 |