Potassium bisulfate → HCID 89955706, compound

HRID 705353Notes

Reaction equation

HRID 705353 reaction equation
[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([CH:21]3[CH2:23][CH2:22]3)[C:10]([N:12]([CH2:17][CH2:18][S:19][CH3:20])[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:6]=2[O:5][C:4]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)#[N:2].[OH:31]S([O-])(=O)=O.[K+]>CO.O>[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([CH:21]3[CH2:23][CH2:22]3)[C:10]([N:12]([CH2:17][CH2:18][S:19]([CH3:20])=[O:31])[S:13]([CH3:16])(=[O:14])=[O:15])=[CH:11][C:6]=2[O:5][C:4]=1[C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)#[N:2]

Participants

5

Reactant 2

HCID 516920Potassium bisulfate3×HCID 89955557HCID 89955557, compound

Product 1

HCID 89955706HCID 89955706, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of Example 12A (0.142 g, 0.320 mmol) in methanol (3 mL) cooled to 0-5° C. was slowly added dropwise a solution of 2 KHSO5.KHSO4.K2SO4 (0.216 g, 0.352 mmol) in water (1 mL). The reaction mixture was stirred for 10 minutes in the ice bath, then at room temperature for 22 hours. The reaction was incomplete by analytical LCMS so additional 2 KHSO5.KHSO4.K2SO4 (111 mg) was added in portions, followed by stirring at room temperature for 2.5 hours. Then more 2KHSO5.KHSO4.K2SO4 (245 mg) was added in portions followed by water (1 mL). The reaction mixture was heated at 50° C. for 4 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and brine. The aqueous phase was further extracted with ethyl acetate (1×). The combined organic extracts were washed with water (2×), dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give a mixture of the title compounds (0.1436 g). MS (ESI+) m/z 494 (M+NH4)+ for sulfone; MS (ESI+) m/z 461 (M+H)+ for sulfoxide.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and brine
  4. extractionThe aqueous phase was further extracted with ethyl acetate (1×)
  5. washThe combined organic extracts were washed with water (2×)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give

Sources & evidence

ORD record
ord-f3e0f1b44909430898b7f03dcb387ee8
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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