Potassium Carbonate → HCID 89955380, compound

HRID 705380Notes

Reaction equation

HRID 705380 reaction equation
[CH:1]1([C:4]2[C:5]([N:25]([CH2:30][CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[S:26]([CH3:29])(=[O:28])=[O:27])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][CH:21]=[CH:22][N:23]=4)[C:8]=3[CH:24]=2)[CH2:3][CH2:2]1.[F:38][C:39]([F:54])([S:50](F)(=[O:52])=[O:51])[C:40]([F:49])([F:48])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:54][C:39]([F:38])([S:50]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:7]3[CH:6]=[C:5]([N:25]([CH2:30][CH2:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:35])=[O:36])[S:26]([CH3:29])(=[O:27])=[O:28])[C:4]([CH:1]4[CH2:3][CH2:2]4)=[CH:24][C:8]=3[C:9]=2[C:19]2[NH:23][CH:22]=[CH:21][N:20]=2)=[CH:13][CH:14]=1)(=[O:52])=[O:51])[C:40]([F:48])([F:49])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 136621547HCID 136621547, compound

Product 1

HCID 89955380HCID 89955380, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 168B (190 mg, 0.349 mmol) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (116 mg, 0.384 mmol), and potassium carbonate (62.8 mg, 0.454 mmol) in N,N-dimethylformamide (3 mL) was stirred for 2 hours and partitioned with ethyl acetate and water. The organic layer was washed with brine twice, dried with sodium sulfate, filtered and concentrated. The resulting solid was triturated with hexane and filtered to give the title compound as a solid (275 mg, 95%). MS (ESI+) m/z 826 (M+H)+.

Workup

  1. custompartitioned with ethyl acetate and water
  2. washThe organic layer was washed with brine twice
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was triturated with hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e4fc4a09e8e143e49857f1a0b4acf5a7
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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