Ibuprofen, (+-)- → 4-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

HRID 18633

Reaction equation

HRID 18633 reaction equation
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].OC1C2N=N[NH:22]C=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:42]1[CH:47]=[CH:46][C:45]([C:48]2[S:52]SC(=S)C=2)=[CH:44][CH:43]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:10]([C:9]1[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:2]([O:1][C:42]2[CH:47]=[CH:46][C:45]([C:48](=[S:52])[NH2:22])=[CH:44][CH:43]=2)=[O:3])=[CH:15][CH:14]=1)[CH:11]([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 3672Ibuprofen, (+-)-HCID 10868DicyclohexylcarbodiimideHCID 3082127Desmethylanethol trithioneHCID 178418300HCID 178418300, compound

Product 1

HCID 250657684-Thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoateYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 1 (ibuprofen, 3.87 g, 18.8 mmol) in 80 mL of dimethylformamide, hydroxybenzotriazole (2.8 g, 20.7 mmol) and DCC (4.27 g, 20.7 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (2, 3.9 g, 28 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 3 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3) was obtained (2.48 g, 40% yield).

Workup

  1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customto remove the solvent
  5. customThe oily residue thus obtained
  6. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
  7. dry with materialthan dried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate (3)
  11. customwas obtained (2.48 g, 40% yield)

Sources & evidence

ORD record
ord-1ca9112d08974993bf3da659e149b590
Source dataset
uspto-grants-2010_06
Patent number
US07741359B2

Linked notes

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