Potassium Carbonate → HCID 59577016, compound

HRID 2041995Notes

Reaction equation

HRID 2041995 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C=O)C>[C:1]([C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:18][CH:19]=2)=[O:13])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59577058HCID 59577058, compound

Product 1

HCID 59577016HCID 59577016, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-{[3-(2-tert-butylphenoxy)azetidin-1-yl]carbonyl}phenol (552 mg, 1.7 mmol) obtained in Example 139 in DMF (20 mL) were added potassium carbonate (1.04 g, 7.5 mmol) and methyl bromoacetate (352 mg, 2.3 mmol), and the mixture was stirred at 70° C. for 3 hr. The reaction mixture was cooled to room temperature, partitioned between ethyl acetate and water, and the ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15-40:60) to give the title compound (578 mg, 69%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washthe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15-40:60)

Sources & evidence

ORD record
ord-553a949bcf4d47deb59583178230b9e7
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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