Potassium Carbonate → HCID 86720064, compound

HRID 1405079Notes

Reaction equation

HRID 1405079 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O>CC(C)=O>[F:30][C:29]([F:32])([F:31])[CH2:28][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 86720064HCID 86720064, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of tert-butyl 3-hydroxyphenylcarbamate (2 g, 9.56 mmol) in acetone (38 mL) were added potassium carbonate (6.61 g, 47.8 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.07 mL, 14.34 mmol). The reaction mixture was heated at 50° C. overnight, cooled and filtered. The filtrate was concentrated, and the residue was dissolved in CH2Cl2, washed with brine, dried over anhydrous sodium sulfate and concentrated to yield the title compound (2.7 g, 97% yield). MS (ES): m/z=314.25 [M+Na]+.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf546023c22844d5bce1f9d2ea8c6a10
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

Loading…