HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ketoprofen → Dexketoprofen
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ketoprofen | HCID 3825 | — |
| Reactant | (S)-3-Methyl-2-phenylbutylamine | HCID 10176271 | — |
| Solvent | Methyl Isobutyl Ketone | HCID 7909 | — |
| Product | Dexketoprofen | HCID 667550 | 65.6% |
Reaction Steps
That is, (±)-2-(3-benzoylphenyl)propionic acid (12.7 g, 50 mmol) was dissolved in MIBK (76 ml) and (S)-(+)-3-methyl-2-phenylbutylamine (4.9 g, 30 mmol) was added dropwise at 40° C. This reaction solution was stirred at 35° C. to 40° C. for one hour, followed by at room temperature for 5 hours and then at 10° C. to 15° C. for one hour. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (30 ml) and dried to give a diastereomer salt (8.34 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine. The yield of the product based on (S)-(+)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 80%. Melting point: 129°-131° C. Optical purity: 94.3% e.e.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05852209 |
| Source dataset | uspto-grants-1998_12 |
| ORD ID | ord-1217c5459dd7497f9a525c87efd59867 |
| Source note | uspto-grants-1998_12 |