Chlorosulfonic acid → HCID 56851160, compound

HRID 1690777Notes

Reaction equation

HRID 1690777 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][N:11]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C@@H:25]([CH3:30])[C:26]([F:29])([F:28])[F:27])=[O:17])[CH2:10]3)[CH2:3][CH2:2]1.[Cl:31][S:32](O)(=[O:34])=[O:33]>ClCCCl>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][N:11]([C:16]([C:18]2[CH:23]=[C:22]([S:32]([Cl:31])(=[O:34])=[O:33])[CH:21]=[CH:20][C:19]=2[O:24][C@@H:25]([CH3:30])[C:26]([F:29])([F:27])[F:28])=[O:17])[CH2:10]3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 56851159HCID 56851159, compound

Product 1

HCID 56851160HCID 56851160, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.2 g (0.47 mmol) [5-(tetrahydro-pyran-4-yl)-1,3-dihydro-isoindol-2-yl]-[2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone in 2 ml of 1,2-dichloroethane was added dropwise to 0.32 ml (4.7 mmol) chlorosulfonic acid under ice bath cooling. The mixture was stirred at room temperature for 30 minutes and then at 55° C. for 30 minutes. The mixture was cooled in an ice bath and quenched by dropwise addition of 2 ml water. The mixture was diluted with dichloromethane. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane extracts were dried over Na2SO4, filtered and concentrated in vacuo. The obtained foam was stirred with ethylacetate. The solid was filtrated. The filtrate was washed twice with a saturated solution of NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo to provide 0.12 g (51%) of the title compound as light yellow foam. MS (m/e): 517.1 [M]+.

Workup

  1. temperaturecooling
  2. waitat 55° C. for 30 minutes
  3. temperatureThe mixture was cooled in an ice bath
  4. customquenched by dropwise addition of 2 ml water
  5. additionThe mixture was diluted with dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted twice with dichloromethane
  8. dry with materialThe combined dichloromethane extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. stirringThe obtained foam was stirred with ethylacetate
  12. filtrationThe solid was filtrated
  13. washThe filtrate was washed twice with a saturated solution of NaHCO3
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-730c7628ed9648cbab7203bf27bc8f65
Source dataset
uspto-grants-2012_04
Patent number
US08153679B2

Reaction notes

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