Potassium Carbonate → HCID 86707726, compound

HRID 1754249Notes

Reaction equation

HRID 1754249 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.C(Cl)Cl.CCCCCC>[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

7

Reactant 3

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

Product 1

HCID 86707726HCID 86707726, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a suspension 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 (121 mg, 0.88 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (112 mg, 0.48 mmol). The reaction mixture was stirred at rt for 14 h. The reaction mixture was diluted with EtOAc (30 mL), and the solution washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated to give the crude residue as a colorless oil. The crude residue was dissolved in DCM/hexane, charged to a 12 g silica gel cartridge which was eluted with a 15 min gradient from 0-100% EtOAc/hexane, followed by 10% MeOH/DCM over 10 min to give Compound 31a (102 mg, 75% yield). 1H NMR (400 MHz, CDCl3-d) 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. washthe solution washed with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude residue as a colorless oil
  6. additioncharged to a 12 g silica gel cartridge which
  7. washwas eluted with a 15 min gradient from 0-100% EtOAc/hexane
  8. waitfollowed by 10% MeOH/DCM over 10 min

Sources & evidence

ORD record
ord-bcb36824dfc04a42b9343740d3863a4c
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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