Ketoprofen → Dexketoprofen

HRID 1459043

Reaction equation

HRID 1459043 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>O1CCCC1>[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 3825KetoprofenHCID 10176271(S)-3-Methyl-2-phenylbutylamine

Product 1

HCID 667550DexketoprofenYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

(±)-2-(3-Benzoylphenyl)propionic acid (12.7 g, 50 mmol) was added to tetrahydrofuran (hereinafter abbreviated to "THF") (45 ml) and dissolved. Then, (S)-(+)-3-methyl-2-phenylbutylamine (4.1 g, 25 mmol) was added dropwise with stirring. After completing the addition, the reaction solution was maintained at 35° C. to 40° C. for one hour, stirred at room temperature for 4 hours, and then cooled to 10° C. The crystal precipitated was filtered, and the filter cake was washed with cold THF (35 ml) and then dried to give a diastereomer salt (5.84 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 56% and the optical purity was 94.3% e.e.

Workup

  1. dissolutiondissolved
  2. additionthe addition
  3. temperaturethe reaction solution was maintained at 35° C. to 40° C. for one hour
  4. stirringstirred at room temperature for 4 hours
  5. customThe crystal precipitated
  6. filtrationwas filtered
  7. washthe filter cake was washed with cold THF (35 ml)
  8. customdried

Sources & evidence

ORD record
ord-a93f0cc35de4414ea15138cb9181163e
Source dataset
uspto-grants-1998_12
Patent number
US05852209

Linked notes

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