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

HRID 18633

반응식

HRID 18633 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1ca9112d08974993bf3da659e149b590
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741359B2

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