Water → HCID 68985776, compound

HRID 475625Notes

Reaction equation

HRID 475625 reaction equation
[F:1][CH:2]([F:29])[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[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])=[O:18])[N:14]=2)=[CH:6][C:5]=1[OH:28].[CH2:30]1CCN2C(=NCCC2)C[CH2:31]1.C(I)C.O>C(O)C.C(OCC)(=O)C>[F:29][CH:2]([F:1])[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[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])=[O:18])[N:14]=2)=[CH:6][C:5]=1[O:28][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68984934HCID 68984934, compound

Product 1

HCID 68985776HCID 68985776, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 60 mg quantity of the compound obtained in Example 229 and 0.2 ml of DBU were dissolved in 4 ml of ethanol, 0.2 ml of ethyl iodide was then added to the obtained solution, and heating and refluxing were conducted for 2 hours. After cooling, water was added to the 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 ethanol, thereby yielding 36 mg of white powdery 3-[2-(4-difluoromethoxy-3-ethoxyphenyl)oxazol-4-yl]-1-(2-ethoxyphenyl)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 ethanol

Sources & evidence

ORD record
ord-3083ac5543ce497f9abe6b2bcca63502
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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