Hydrochloric Acid → 3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acid

HRID 1269583Notes

Reaction equation

HRID 1269583 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:14]=2)=[C:7]([Cl:30])[CH:6]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[CH:6]=[C:7]([Cl:30])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18448782HCID 18448782, compound

Product 1

HCID 102977453,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acidYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl{3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyramidophenoxy]phenyl}acetate(10 mg, 0.02 mmol), LiOH (2 mL, 1N) and THF (1 mL) was stirred at room temperature for 16 hours. The reaction mixture was poured into an aqueous solution of hydrochloric acid (1N). The aqueous layer was extracted with ethyl acetate, and the combined organic layers was washed with water, dried over MgSO4, filtered, and concentrated at reduced pressure to give 3.2 mg (35%) of 3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acid, m/z 452.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe combined organic layers was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-6bd1486080c04a999e30edfbea4179be
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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