Water → HCID 57855772, compound

HRID 475622Notes

Reaction equation

HRID 475622 reaction equation
[F:1][CH:2]([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)=[CH:6][C:5]=1[OH:26].N12CCCN=C1C[CH2:32][CH2:31][CH2:30][CH2:29]2.BrCCC=C.O>C(O)C.C(OCC)(=O)C>[CH2:32]([O:26][C:5]1[CH:6]=[C:7]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:18])[N:14]=2)[CH:8]=[CH:9][C:4]=1[O:3][CH:2]([F:1])[F:27])[CH2:31][CH:30]=[CH2:29]

Participants

7

Reactant 4

HCID 962WaterHCID 21241Homoallyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68984745HCID 68984745, compound

Product 1

HCID 57855772HCID 57855772, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

An 80 mg quantity of the compound obtained in Example 327 and 0.09 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 2 ml of ethanol, and 80 mg of 4-bromo-1-butene was then added to the obtained solution, and heating and refluxing were conducted overnight. After cooling, water was added to the obtained reaction mixture, and ethyl acetate extraction was performed. The organic layer was washed twice with water, concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1). The obtained crystals were recrystallized from aqueous 80% ethanol, thereby yielding 22 mg of white powdery 3-[2-(3-but-3-enyloxy-4-difluoromethoxyphenyl)-oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one

Workup

  1. temperatureheating
  2. temperaturerefluxing
  3. temperatureAfter cooling
  4. washThe organic layer was washed twice with water
  5. concentrationconcentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)
  7. customThe obtained crystals were recrystallized from aqueous 80% ethanol

Sources & evidence

ORD record
ord-a73b7907ba5a4c81a449fa9ec8f41489
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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