2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 86635795, compound

HRID 605581Notes

Reaction equation

HRID 605581 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[N:13]=[C:12]2[C:23](=[O:37])[N:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[N:25]=[C:11]2[CH:10]=1.[F:38][C:39]([F:50])([F:49])[CH2:40]OS(C(F)(F)F)(=O)=O.C([O-])(O)=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:40][C:39]([F:50])([F:49])[F:38])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[N:13]=[C:12]2[C:23](=[O:37])[N:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:29][CH:28]=3)[N:25]=[C:11]2[CH:10]=1

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 136338470HCID 136338470, compound

Product 1

HCID 86635795HCID 86635795, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.45 g of the compound obtained in stage A of Example 18, 0.38 g of 2,2,2-trifluoroethyltrifluoromethanesulfonate and 0.28 g of NaHCO3 in 14 ml of EtOH is refluxed for 2 hours. The reaction mixture is concentrated under vacuum, the residue is taken up with water, the mixture is extracted with DCM, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, elution being carried out with a mixture of DCM/EtOAc (100/30; V/V). 0.145 g of the expected compound is obtained after crystallization from iso ether.

Workup

  1. temperatureis refluxed for 2 hours
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionthe mixture is extracted with DCM
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica gel, elution
  7. additionbeing carried out with a mixture of DCM/EtOAc (100/30; V/V)

Sources & evidence

ORD record
ord-54f0c8c422894265a32cbfb42aa76e47
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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