Ibuprofen, (+-)- → HCID 66909871, compound

HRID 1879807Notes

Reaction equation

HRID 1879807 reaction equation
C([O-])(=O)CCC.[CH3:7][CH:8]([CH3:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:20])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([O:35][C:36](=[O:41])[CH2:37][CH2:38][CH2:39]Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C.CCOC(C)=O.CCCCCCC>[CH3:7][CH:8]([CH3:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:20])[C:17]([O:19][CH2:39][CH2:38][CH2:37][C:36]([O:35][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:41])=[O:18])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 3672Ibuprofen, (+-)-2×HCID 11430Potassium Carbonate2×HCID 104775ButyrateHCID 3832489Benzyl 4-bromobutanoate

Product 1

HCID 66909871HCID 66909871, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
90 °C

Procedure

Benzyl 4-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)butanoate was synthesized from benzyl-4-bromo)butanoate, 2-[4-(2-methylpropyl)phenyl]propanoic acid and potassium carbonate. To a solution of benzyl-4-bromobutanoate (2.0 g, 7.8 mmol) in acetonitrile (20 ml) at ambient temperature was added potassium carbonate (1.13 g, 8.2 mmol) and 2-[4-(2-methylpropyl)phenyl]propanoic acid (1.6 g, 7.8 mmol). The reaction was heated to 90° C. for 18 hours and monitored by TLC (4:1 heptane:EtOAc) The mixture was allowed to cool to room temperature and concentrated in vacuo. The crude product was partitioned between water and EtOAc and the organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with heptane:EtOAc (4:1, v:v) and isolated as a clear, colorless oil (2.5 g, 84% yield). 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 7.30-7.46 (5H, m), 7.02-7.23 (4H, m), 5.11 (2H, s), 3.99-4.21 (2H, m), 3.68 (1H, q, 7.2 Hz), 2.43 (2H, d, 7.2 Hz), 2.27-2.39 (2H, m), 1.73-2.04 (3H, m), 1.48 (3H, d, 7.2 Hz) 0.89 (6H, d, 6.6 Hz).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude product was partitioned between water and EtOAc
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by silica column chromatography
  9. washeluting with heptane:EtOAc (4:1, v:v)

Sources & evidence

ORD record
ord-9a8cc8c108e3427eb292da599caea718
Source dataset
uspto-grants-2012_11
Patent number
US08318705B2

Reaction notes

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