HCID 86612349, compound → HCID 23114347, compound

HRID 2376412Notes

Reaction equation

HRID 2376412 reaction equation
C([N:3]([C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:13]=2[C:26]=1[CH3:27])[C:4](=[O:8])[C:5]([O-:7])=O)C.[C:30]([Mg]Cl)([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:14]2[C:13]3[C:26]([CH3:27])=[C:9]([NH:3][C:4](=[O:8])[C:5](=[O:7])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=3[O:16][CH2:15]2)=[CH:18][CH:19]=1)([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 86612349HCID 86612349, compoundHCID 178418310HCID 178418310, compound

Product 1

HCID 23114347HCID 23114347, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)oxamate (100 mg, 0.25 mmol) obtained in Example 15 in THF (3 ml) was added dropwise at 0° C. under an argon atmosphere tert-butylmagnesium chloride (2.0 M THF solution, 0.26 mL, 0.5 mmol) and the mixture was stirred for 30 minutes. After the reaction solution was stirred at room temperature for 1 hour, the reaction solution was added to ice and the product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from ethyl acetate-hexane to obtain 29 mg (yield: 28%) of the title compound. Melting point: 142-143° C.

Workup

  1. stirringAfter the reaction solution was stirred at room temperature for 1 hour
  2. additionthe reaction solution was added to ice
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-17dac4b1c7534fbe882e3fd938aed2b9
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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