Xenon difluoride → HCID 178516169, compound

HRID 1881962Notes

Reaction equation

HRID 1881962 reaction equation
[CH:1]1([C:5]([C:7]2[NH:11][C:10]([CH:12]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH:29]4[CH2:31][CH2:30]4)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:13][C@H:14]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]3)=[N:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[Xe](F)[F:33]>C(#N)C>[CH:1]1([C:5]([C:7]2[NH:11][C:10]([CH:12]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH:29]4[CH2:30][CH2:31]4)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:13][C@H:14]3[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]3)=[N:9][C:8]=2[F:33])=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 83674Xenon difluorideHCID 59331581HCID 59331581, compound

Product 1

HCID 178516169HCID 178516169, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution (16 mL) of (3R)-3-{2-[5-(cyclobutylcarbonyl)-1H-imidazol-2-yl]-2-[4-(cyclopropylsulfonyl)phenyl]ethyl}cyclopentanone (0.720 g) in acetonitrile was added xenon difluoride (0.552 g), and the mixture was heated under reflux for 4 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio), and recrystallized from diethyl ether-hexane to give the title compound (0.035 g, yield 5%) as colorless crystals. melting point 85-88° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively 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 (ethyl acetate:hexane=30:70-100:0, volume ratio)
  8. customrecrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-a771f5b0b5d14435bd2edf2eb290a684
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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