HCID 86612349, compound → HCID 23114141, compound

HRID 2376415Notes

Reaction equation

HRID 2376415 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-])=[O:6])C.[C:30]([Mg]Cl)([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[OH:6][CH:5]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:4]([NH: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:18]=[CH:19][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=3)[C:13]=2[C:26]=1[CH3:27])=[O:8]

Participants

4

Reactant 2

HCID 86612349HCID 86612349, compoundHCID 178418310HCID 178418310, compound

Product 1

HCID 23114141HCID 23114141, compoundYield 38%

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 (500 mg, 1.26 mmol) obtained in Example 15 in THF (10 mL) was added dropwise at 0° C. under an argon atmosphere tert-butylmagnesium chloride (2.0 M THF solution, 1.9 mL, 3.78 mmol) and the mixture was stirred for 30 minutes. After the reaction solution was warmed to room temperature and was stirred at the same 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 194 mg (yield: 38%) of the title compound as a diastereomer mixture. Melting point: 165-166° C.

Workup

  1. stirringwas stirred at the same 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-7138394355c147f981d559a1db492bce
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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