Ibuprofen, (+-)- → HCID 9861357, compound

HRID 1872788Notes

Reaction equation

HRID 1872788 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].[C:16]([O:21][CH2:22]Cl)(=[O:20])[CH2:17][CH2:18][CH3:19].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[C:16]([O:21][CH2:22][O:3][C:2](=[O:1])[CH:4]([CH3:5])[C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:14][CH:15]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 3672Ibuprofen, (+-)-HCID 8471TriethylamineHCID 2725008Chloromethyl butanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 9861357HCID 9861357, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of ibuprofen (10.16 g, 49 mmol) and chloromethyl butyrate (6.80 g, 1 eq.) in dry dimethylformamide (20 mL), under nitrogen, was dropwise added triethylamine (8.5 mL, 6 g, 1.2 eq). The mixture was heated at 70° C. for four hours, during which time a large amount of precipitate formed; thin layer chromatography (TLC: ethyl acetate:hexane 1:1) showed that all of the acid had reacted. The precipitate was filtered and washed with ethyl acetate. The filtrate was partitioned between water and ethyl acetate. The aqueous phase was washed with a small amount of ethyl acetate and the combined organic phase was washed with water (3 x), 5% solution of sodium bicarbonate (2 x), and brine (2 x), dried with magnesium sulfate and evaporated to give the crude product as a colorless oil (11.6 g). The crude product was distilled at 170° C./1 mm Hg. The pure product was obtained as a colorless oil (8.7 g, 58% yield).

Workup

  1. customformed
  2. customhad reacted
  3. filtrationThe precipitate was filtered
  4. washwashed with ethyl acetate
  5. customThe filtrate was partitioned between water and ethyl acetate
  6. washThe aqueous phase was washed with a small amount of ethyl acetate
  7. washthe combined organic phase was washed with water (3 x), 5% solution of sodium bicarbonate (2 x), and brine (2 x)
  8. dry with materialdried with magnesium sulfate
  9. customevaporated
  10. customto give the crude product as a colorless oil (11.6 g)
  11. distillationThe crude product was distilled at 170° C./1 mm Hg

Sources & evidence

ORD record
ord-38bc0cc62ebc4d6cbec2af040eaec92a
Source dataset
uspto-grants-2000_08
Patent number
US06110955

Reaction notes

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