Potassium Carbonate → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

HRID 418065Notes

Reaction equation

HRID 418065 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].[I:30][C:31]1[CH:32]=[C:33]([OH:41])[CH:34]=[C:35]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CC(C)=O.CCOC(C)=O>[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][O:41][C:33]2[CH:34]=[C:35]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:36]=[C:31]([I:30])[CH:32]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 578630243-Iodo-5-methanesulfonyl-phenol

Product 1

HCID 578630374-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl EsterYield 97.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (3.79 g, 8.05 mmol), 3-iodo-5-methanesulfonyl-phenol (2.0 g, 6.71 mmol) in dimethylformamide (40 mL) and acetone (80 mL) was added potassium carbonate (9.25 g, 67.1 mmol). The resulting suspension was heated at 70° C. for 24 h. Then, the reaction mixture was cooled to room temperature, diluted with EtOAc and washed with 10% HCl and water. Then, the combined organic extracts were washed with brine. The organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which was purified by using an ISCO 120 g column. The desired compound was eluted with 40% EtOAc-Hexanes. The desired fractions were combined and evaporated under reduced pressure to afford 4.5 g (97%) of title compound as a colorless oil. HR-ES(+) m/e calcd for C30H41O8SI (M+Na)+ 711.1459, found 711.1465.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. washwashed with 10% HCl and water
  3. washThen, the combined organic extracts were washed with brine
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product which
  7. customwas purified
  8. washThe desired compound was eluted with 40% EtOAc-Hexanes
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-aca359d0761e4ab3ba02343a9cd17a1b
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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