HCID 22917831, compound → HCID 22917835, compound

HRID 259918

Reaction equation

HRID 259918 reaction equation
F[C:2](F)(F)[C:3](F)(F)[C:4](F)(F)[C:5](F)(F)S([O-])(=O)=O.[K+].[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]([S:30]([O-:33])(=[O:32])=[O:31])[CH3:29])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]>CC(C)=O>[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]([S:30]([O-:33])(=[O:31])=[O:32])[CH3:29])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20].[CH2:2]([N+:19]([CH2:22][CH2:23][CH2:24][CH3:28])([CH2:25][CH2:24][CH2:28][CH3:29])[CH2:23][CH2:22][CH2:27][CH3:26])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 22917831HCID 22917831, compoundHCID 23675274Potassium perfluorobutanesulfonate

Product 1

HCID 22917835HCID 22917835, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

5.2 g of potassium nonafluorobutanesulphonate dissolved in 12 cm3 of acetone are added to a solution of 10.5 g of a mixture of the A and B forms (about 15/85 in moles) of N-benzylquininium 1-(3-nitrophenyl)ethanesulphonate in 16 cm3 of acetone. The insoluble product is filtered off and then dissolved in 9 cm3 of water. 8.4 cm3 of an aqueous 1N hydrochloric acid solution and 1.15 g of (R)-(-)-phenylglycinol are added. The solution obtained is concentrated to dryness under reduced pressure (2.7 kPa) at 50° C. The residue obtained is extracted with 3 times 15 cm3 of acetonitrile under reflux. The organic phases are combined and concentrated to about 7 cm3 ; after cooling, the crystals are filtered off and dissolved in 7.5 cm3 of an aqueous 1N sodium hydroxide solution. The solution obtained is washed with 8 times 25 cm3 of diethyl ether, after which 60 cm3 of an aqueous 0.5M solution of potassium dihydrogenphosphate and 2.3 g of tetra-n-butylammonium hydrogensulphate are added. The mixture is extracted with 3 times 30 cm3 of methylene chloride. The combined organic phases are dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 2.8 g of the laevorotatory isomer of tetra-n-butylammonium 1-(3-nitrophenyl)ethanesulphonate are thus obtained in the form of an oil which is used as such in the subsequent syntheses.

Workup

  1. filtrationThe insoluble product is filtered off
  2. dissolutiondissolved in 9 cm3 of water
  3. addition8.4 cm3 of an aqueous 1N hydrochloric acid solution and 1.15 g of (R)-(-)-phenylglycinol are added
  4. customThe solution obtained
  5. concentrationis concentrated to dryness under reduced pressure (2.7 kPa) at 50° C
  6. customThe residue obtained
  7. extractionis extracted with 3 times 15 cm3 of acetonitrile
  8. temperatureunder reflux
  9. concentrationconcentrated to about 7 cm3
  10. temperatureafter cooling
  11. filtrationthe crystals are filtered off
  12. dissolutiondissolved in 7.5 cm3 of an aqueous 1N sodium hydroxide solution
  13. customThe solution obtained
  14. washis washed with 8 times 25 cm3 of diethyl ether
  15. additionafter which 60 cm3 of an aqueous 0.5M solution of potassium dihydrogenphosphate and 2.3 g of tetra-n-butylammonium hydrogensulphate are added
  16. extractionThe mixture is extracted with 3 times 30 cm3 of methylene chloride
  17. dry with materialThe combined organic phases are dried over magnesium sulphate
  18. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-4645baddb7264d5393abc18a22ebcc62
Source dataset
uspto-grants-1996_06
Patent number
US05523469

Linked notes

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