Potassium Carbonate → HCID 71279219, compound

HRID 1621139Notes

Reaction equation

HRID 1621139 reaction equation
C(OC([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O>CN(C=O)C>[C:16]1([C:13]2[N:12]=[C:11]([CH2:10][CH2:9][NH:8][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[N:15]([CH2:41][C:42]([F:45])([F:44])[F:43])[N:14]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 71279243HCID 71279243, compound

Product 1

HCID 71279219HCID 71279219, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[2-Bis(tert-butoxycarbonyl)aminoethyl]-3-phenyl-[1,2,4]triazole (200 mg, 515 μmol; example 22, step 1) was dissolved in DMF (3.57 mL) and potassium carbonate (157 mg, 1.14 mmol) was added at RT. The mixture was stirred for 20 min, 2,2,2-trifluoroethyl trifluoromethanesulfonate (165 mg, 710 μmol) was added and stirring was continued at RT overnight. The reaction mixture was extracted with ethyl acetate (40 mL) and washed with water (3×20 mL) and brine (1×20 mL). The aqueous layers were back-extracted with ethyl acetate (40 mL) and the combined organic layer was dried over MgSO4 and concentrated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as white solid (140 mg, 378 μmol, 73.4%).

Workup

  1. stirringstirring
  2. waitwas continued at RT overnight
  3. extractionThe reaction mixture was extracted with ethyl acetate (40 mL)
  4. washwashed with water (3×20 mL) and brine (1×20 mL)
  5. extractionThe aqueous layers were back-extracted with ethyl acetate (40 mL)
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe product was obtained
  9. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-cb040985cbb94f89a8d31be7af8f0e27
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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