N-Fluorobenzenesulfonimide → HCID 11516742, compound

HRID 229376Notes

Reaction equation

HRID 229376 reaction equation
C(=O)(OCC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:23])=[C:19]([F:22])[CH:20]=3)[N:15]3[CH:24]=[CH:25][CH:26]=[C:14]3[CH:13]2[CH3:27])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:42])(=O)=O)=CC=1>C(#N)C>[F:42][C:24]1[N:15]2[C:16]3[C:21]([N:12]([S:9]([C:6]4[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=4)(=[O:10])=[O:11])[CH:13]([CH3:27])[C:14]2=[CH:26][CH:25]=1)=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3

Participants

4

Reactant 2

HCID 588007N-FluorobenzenesulfonimideHCID 69070333HCID 69070333, compound

Product 1

HCID 11516742HCID 11516742, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 250 ml round bottom flask equipped with condenser was added 3.2 g (7.2 mmol) of the product from Example 9, 3.5 g (10.8 mmol) of N-fluorobenzenesulfonimide and 100 ml of acetonitrile. The solution was heated to reflux for 4 hours. At the end of this time the solution was concentrated and the residue washed with saturated potassium carbonate solution and extracted with ethyl acetate (3×50 ml). The organic layers were combined dried (MgSO4) and concentrated and the resulting crude material chromatographed with 20% ethyl acetate:hexane to yield 1.5 g of material. The enantiomers can be separated (see below) or this material can be hydrolyzed by dissolving in 50 ml of MeOH and 2 ml of 2N NaOH added. After 0.5 hr the solution was concentrated and neutralized with 2N HCL then extracted with ethyl acetate (3×50 ml). The organic layers were combined dried (MgSO4) and concentrated and the solid once again chromatographed with 40% ethyl acetate:hexane. The solid so obtained was recrystallized from ethyl acetate:hexane to yield 0.45 g of product, mp 184-186° C.

Workup

  1. customTo a 250 ml round bottom flask equipped with condenser
  2. temperatureThe solution was heated
  3. temperatureto reflux for 4 hours
  4. concentrationAt the end of this time the solution was concentrated
  5. washthe residue washed with saturated potassium carbonate solution
  6. extractionextracted with ethyl acetate (3×50 ml)
  7. dry with materialThe organic layers were combined dried (MgSO4)
  8. concentrationconcentrated
  9. customthe resulting crude material chromatographed with 20% ethyl acetate

Sources & evidence

ORD record
ord-e825d105945e4f6e9fa4039769f7ebba
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

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