HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-Amino-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]-2-phenylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | {[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester | HCID 69848144 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | 2-Amino-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]-2-phenylacetamide | HCID 22713739 | — |
Reaction Steps
{[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester (1.24 g; 2.2 mmol) was dissolved in excess, neat acetic acid saturated with HCl(g) (20 mL). After stirring 30 min at room temperature, the solution was concentrated to dryness by rotary evaporation. Acetic acid was removed from the resulting solid by consecutive dissolution in, and drying from, acetonitrile (thrice) and then diethyl ether (once). The solid was dissolved in 25% (v/v) isopropyl alcohol in chloroform, washed with saturated NaHCO3(aq), and dried by rotary evaporation to yield the desired product in 97% isolated yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06743794B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-adc3eccee718488ca44746e865800b39 |
| Source note | uspto-grants-2004_06 |