Potassium Carbonate → 3-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl Ester

HRID 1670096Notes

Reaction equation

HRID 1670096 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[C:30]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[C:40]([OH:42])[CH:39]=[C:38]([Br:43])[CH:37]=1)([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CC(C)=O.O.Cl>[C:30]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[C:40]([O:42][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])[C:10]=2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:39]=[C:38]([Br:43])[CH:37]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 673385233-Bromo-5-hydroxy-benzoic Acid tert-butyl Ester

Product 1

HCID 673397313-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl EsterYield 99%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (9.48 g, 20.1 mmol), 3-bromo-5-hydroxy-benzoic acid tert-butyl ester (5.0 g, 18.3 mmol) in N,N-dimethylformamide (100 mL) and acetone (200 mL) was added potassium carbonate (25.3 g, 183 mmol) at room temperature. The resulting suspension was heated to 70° C. for 24 h. Then, the reaction mixture was cooled to room temperature and diluted with water and 10% aq. HCl. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with water and brine solution. The organic layers were dried over anhydrous sodium sulfate and removal of the solvent under reduced pressure gave the crude product which was purified on a silica gel column eluting with 0-20% ethyl acetate in hexanes to afford the title compound (12 g, 99%) as a colorless oil.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. extractionThe organic compound was extracted into ethyl acetate
  3. washthe combined organic extracts were washed with water and brine solution
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate and removal of the solvent under reduced pressure
  5. customgave the crude product which
  6. customwas purified on a silica gel column
  7. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-afcc63add37940bf8fee2ff2d1d710ce
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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