Potassium hydroxy sulfite → HCID 56650969, compound

HRID 1961555Notes

Reaction equation

HRID 1961555 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:33]([F:36])([F:35])[F:34])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([F:32])[CH2:24][N:23]([C:25]([CH:27]5[CH2:30][S:29](=[O:31])[CH2:28]5)=[O:26])[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[OH:37]OS([O-])=O.[K+]>CO.O>[Cl:9][C:6]1[CH:5]=[C:4]([C:10]2([C:33]([F:35])([F:36])[F:34])[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:21]4([F:32])[CH2:22][N:23]([C:25]([CH:27]5[CH2:28][S:29](=[O:37])(=[O:31])[CH2:30]5)=[O:26])[CH2:24]4)=[CH:19][CH:20]=3)[CH2:11]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 56650968HCID 56650968, compound

Product 1

HCID 56650969HCID 56650969, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (3-(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidin-1-yl)(1-oxidothietan-3-yl)methanone (30 mg) in methanol (2 mL) was added to a solution of oxone (160 mg) in water (1 mL) cooled with an ice bath. Reaction allowed to warm slowly to ambient then stirred at ambient temperature for 16 hours. Majority of methanol removed under reduced pressure then remaining aqueous extracted with DCM (2×5 mL). Organic phase collected and condensed. The crude material was adsorbed on silica and chromatographed on a 4 g silica column, eluting with a gradient of 0% to 100% ethyl acetate in heptane. Fractions containing the desired material were combined and concentrated. Placing the flask on high vacuum overnight resulted in formation of a white foam. Yield 15.7 mg (51%). 1H NMR (DMSO-D6) δ 7.82 (m, 4H), 7.69 (m, 2H), 4.67 (d, 2H), 4.46-4.29 (m, 8H), 3.56-3.43 (m, 1H). LC/MS retention time=3.455 minutes, MS calculated for (C23H17Cl2F5N2O4S), 582.02; nd M+H+.

Workup

  1. temperaturecooled with an ice bath
  2. customReaction
  3. temperatureto warm slowly
  4. customMajority of methanol removed under reduced pressure
  5. extractionremaining aqueous extracted with DCM (2×5 mL)
  6. customOrganic phase collected
  7. customcondensed
  8. customchromatographed on a 4 g silica column
  9. washeluting with a gradient of 0% to 100% ethyl acetate in heptane
  10. additionFractions containing the desired material
  11. concentrationconcentrated
  12. customon high vacuum overnight
  13. customresulted in formation of a white foam

Sources & evidence

ORD record
ord-cbe75127e41f411184e4aabaf88509bb
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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