Cesium carbonate → HCID 23447918, compound

HRID 381288Notes

Reaction equation

HRID 381288 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 mixture of 2.83 g of Compound 6A, 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 while stirring. The solvent was evaporated off at reduced pressure, 90 mL of brine was added to the residue, and the mixture was extracted with ethyl acetate (3×40 mL). The organic layer was washed with water (3×20 mL) and of brine (20 mL) and dried over sodium sulphate. The solvent was removed at reduced pressure and the residue purified by flash chromatography in a petroleum ether/ethyl acetate gradient (95:5 to 80:20). The solvents were removed in vacuo to yield 1.86 g (52%) of Compound 6B as a white solid. M.p. (98) 102-105° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was evaporated off at reduced pressure, 90 mL of brine
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (3×40 mL)
  5. washThe organic layer was washed with water (3×20 mL) and of brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed at reduced pressure
  8. customthe residue purified by flash chromatography in a petroleum ether/ethyl acetate gradient (95:5 to 80:20)
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a1ef52dfd64347f3ab8271483321837a
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

Loading…