Cesium carbonate → HCID 23447918, compound

HRID 840114Notes

Reaction equation

HRID 840114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC(S(O[CH2:39][C:40]([F:43])([F:42])[F:41])(=O)=O)=CC=1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH2:39][C:40]([F:43])([F:42])[F:41])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 23447878HCID 23447878, compound

Product 1

HCID 23447918HCID 23447918, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 2.83 g of Compound 4A, 6.05 g of cesium carbonate and 2.95 g of 2,2,2-trifluoroethyl p-toluenesulphonate in 60 mL of acetonitrile was refluxed for 16 hours. The solvent was evaporated at reduced pressure. 90 mL of brine was added to the residue and the mixture was extracted with 3×40 mL of ethyl acetate. The organic layer was washed with 3×20 mL of water and 20 mL of brine, and dried over sodium sulphate. The solvent was removed at reduced pressure and the residue purified by flash chromatography (petroleum ether/ethyl acetate gradient 95:5 to 80:20). The solvents were removed in vacuo to give 1.86 g (52%) of Compound 4B as a white solid. M.p. (98) 102-105° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was evaporated at reduced pressure
  3. addition90 mL of brine was added to the residue
  4. extractionthe mixture was extracted with 3×40 mL of ethyl acetate
  5. washThe organic layer was washed with 3×20 mL of water and 20 mL of brine
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed at reduced pressure
  8. customthe residue purified by flash chromatography (petroleum ether/ethyl acetate gradient 95:5 to 80:20)
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-faa9b4bce5254b97985c6a8125c22153
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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