Ketoprofen → (R)-Ketoprofen

HRID 1459040Notes

Reaction equation

HRID 1459040 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)[C@H](C1C=CC=CC=1)CN>CC(CC(C)=O)C>[C:1]([C:9]1[CH:10]=[C:11]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3825Ketoprofen2×HCID 10249763HCID 10249763, compound

Product 1

HCID 180540(R)-KetoprofenYield 47.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
40 °C

Procedure

(±)-2-(3-Benzoylphenyl)propionic acid (13.55 g, 53.3 mmol) was dissolved in MIBK (67.5 g) with heating. Then, (R)-(-)-3-methyl-2-phenylbutylamine (3.92 g, 24 mmol), 0.45 equivalent based on the amount of (±)-2-(3-benzoylphenyl)propionic acid, was added dropwise with stirring at 40°C. After completing the addition, the reaction solution was stirred at 40°C. for 2 hours, followed by stirring at room temperature for 6 hours and then at 10°C. for 2 hours. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (25 ml) and dried to give a diastereomer salt (6.48 g) of (R)-(-)-2-(3-benzoylphenyl)propionic acid with (R)-(-)-3-methyl-2-phenylbutylamine. The yield of the product based on (R)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 58.3%.

Workup

  1. temperaturewith heating
  2. additionwas added dropwise
  3. additionthe addition
  4. stirringthe reaction solution was stirred at 40°C. for 2 hours
  5. stirringby stirring at room temperature for 6 hours
  6. customThen, the crystal precipitated
  7. filtrationwas filtered
  8. washthe filter cake was washed with cold MIBK (25 ml)
  9. customdried

Sources & evidence

ORD record
ord-6432376b34244a11901a4ce345329261
Source dataset
uspto-grants-1998_12
Patent number
US05852209

Reaction notes

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