Potassium Carbonate → HCID 86707726, compound

HRID 1190831Notes

Reaction equation

HRID 1190831 reaction equation
[CH3:1][C:2]1([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:29][C:30]([F:33])([F:32])[F:31])(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6](=[O:7])[N:5]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:4](=[O:8])[NH:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 17986967HCID 17986967, compound

Product 1

HCID 86707726HCID 86707726, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetate (100 mg, 0.44 mmol) in DMF (1 mL) was added potassium carbonate (120 mg, 0.88 mmol) followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.48 mmol) and the reaction mixture stirred at rt overnight. The mixture was diluted with EtOAc (30 mL) and washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexane followed by 10% MeOH/DCM to give Compound 26c (102 mg, 75% yield). 1H NMR (400 MHz, CDCl3) δ 6.12 (br. s., 1H), 4.14 (q, J=8.5 Hz, 2H), 2.78-2.62 (m, 2H), 1.52 (s, 3H), 1.45 (s, 9H).

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-100% EtOAc/hexane

Sources & evidence

ORD record
ord-0e5d1ab935da455485d00eb3f38bf3bb
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

Loading…