N-Fluorobenzenesulfonimide → HCID 10189127, compound

HRID 896679Notes

Reaction equation

HRID 896679 reaction equation
[OH:1][C:2]([CH3:41])([CH3:40])[C:3](=[O:39])[CH:4]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([S:25]([CH3:28])(=[O:27])=[O:26])([CH3:24])[CH3:23])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1.CC(C)([O-])C.[K+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:58])(=O)=O)=CC=1>C1COCC1.CN(C=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[F:58][C:4]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)([C:3](=[O:39])[C:2]([OH:1])([CH3:41])[CH3:40])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([S:25]([CH3:28])(=[O:26])=[O:27])([CH3:23])[CH3:24])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1

Participants

7

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 9960211HCID 9960211, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10189127HCID 10189127, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of Example 1 (200 mg, 0.34 mmol) in THF/DMF (1:1, 10 mL) at 0° C. was added potassium tert-butoxide (1M, THF, 0.34 mL, 0.34 mmol) dropwise. After 15 min, N-fluorobenzene sulfonimide (212 mg, 0.73 mmol) was added and the reaction mixture stirred for 2 h at 21° C. The resulting mixture was diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with toluene/acetone, 80:20) provided the title compound.

Workup

  1. washThe organic extracts were washed (H2O), (brine),
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification
  6. washby flash chromatography (eluting with toluene/acetone, 80:20)

Sources & evidence

ORD record
ord-3c2288d729d4483282c3ec3537a06fe4
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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