Sodium Hydroxide → HCID 57586446, compound

HRID 420355Notes

Reaction equation

HRID 420355 reaction equation
C([O:3][C:4](=[O:37])[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:21][C:22]2[CH:27]=[C:26]([Br:28])[CH:25]=[C:24]([Br:29])[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])C.[OH-].[Na+]>C(O)C>[C:32]([CH2:31][CH2:30][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([Br:29])[CH:25]=[C:26]([Br:28])[CH:27]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:37])=[O:3])([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57586569HCID 57586569, compound

Product 1

HCID 57586446HCID 57586446, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
52.5 °C

Procedure

To a solution of 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (1.5 g, 2.33 mmol) in ethanol (30 mL) was added aqueous 1 N sodium hydroxide (25 mL) at room temperature. The resulting suspension was heated to 50-55° C. and the mixture was stirred for 3 h. Then, the reaction mixture was concentrated and the residue was diluted with water (20 mL) and extracted with diethyl ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1 N hydrochloric acid and the organic compound was extracted into ethyl acetate (2×50 mL). The combined ethyl acetate extracts were washed with brine solution (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product which was purified by using an ISCO 40 g column, eluting with 0-100% ethyl acetate/hexanes to isolate 4-{2-(2-carboxy-ethyl)-3-[6-(3,5-dibromo-phenoxy)-hexyl]-phenoxy}-butyric acid (1.26 g, 92%) as a white solid: ES(+)-HRMS m/e calculated for C25H30Br2O6 (M+Na)+ 607.0301, found 607.0298.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. additionthe residue was diluted with water (20 mL)
  3. extractionextracted with diethyl ether (50 mL)
  4. customto remove any neutral impurities
  5. extractionthe organic compound was extracted into ethyl acetate (2×50 mL)
  6. washThe combined ethyl acetate extracts were washed with brine solution (50 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product which
  11. customwas purified
  12. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f1baeb2f429b4925a7f289964929bda9
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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