Water → HCID 86612360, compound

HRID 2376529Notes

Reaction equation

HRID 2376529 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]2[C:15]3[C:16]([CH3:30])=[C:17]([NH:22][C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]([CH3:21])=[C:19]([CH3:20])[C:14]=3[O:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9].[CH2:31]([O:33][C:34](=[O:37])[CH2:35]Br)[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[K+]>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([NH:22][C:17]1[C:18]([CH3:21])=[C:19]([CH3:20])[C:14]2[O:13][CH2:12][CH:11]([C:4]3[CH:5]=[CH:6][C:7]([CH:8]([CH3:10])[CH3:9])=[C:2]([CH:3]=3)[O:1][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37])[C:15]=2[C:16]=1[CH3:30])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23114199HCID 23114199, compound

Product 1

HCID 86612360HCID 86612360, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixed solution of N-(3-(3-hydroxy-4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.22 mmol) obtained in Example 186, ethylbromoacetate (245 mg, 1.47 mmol), potassium carbonate (253 mg, 1.83 mmol) and potassium iodide (10 mg) in acetone (10 mL) was heated for 16 hours under an argon atmosphere. Water was added to the reaction solution and the product was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 548 mg (yield: 91%) of the title compound. Melting point: 149-150° C. (ethyl acetate-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f237a642d5a44bd899a90381a33d648a
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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