HCID 53677498, compound → HCID 13596549, compound

HRID 248778Notes

Reaction equation

HRID 248778 reaction equation
[CH3:1][Li].[CH2:3]([O:5][C:6](=[O:21])[C@@:7]([F:20])([CH3:19])[CH2:8]S(C1C=CC(C)=CC=1)(=O)=O)[CH3:4]>CCOCC.[Cu](I)I>[CH2:3]([O:5][C:6](=[O:21])[C@:7]([F:20])([CH3:19])[CH2:8][CH3:1])[CH3:4]

Participants

5

Reactant 2

HCID 53677498HCID 53677498, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 13596549HCID 13596549, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4.8 g (0.025 mol) of copper iodide was added to 10 ml of dried ether, which was cooled to -25°~-30° C. under a nitrogen gas flow and thereafter 36 ml of methyl lithium was added dropwise thereto. Then, 3.8 g (0.01 mol) of (S)-(-)-3-(p-toluenesulfonyl)-2-fluoro-2-methylpropionic acid monoethyl ester dissolved in 10 ml of dried ether at -15°~-20° C. was added dropwise thereto, which was stirred at 0°~5° C. for 10 hours. After the completion of the reaction, the precipitate was removed by filtration and then the filtrate was washed with 1 normal hydrochloric acid and further with water and dried on anhydrous magnesium sulfate. After the removal of magnesium sulfate by filtration, the solvent was distilled off and the residue as it is was used for the following reaction.

Workup

  1. temperaturewas cooled to -25°~-30° C. under a nitrogen gas flow
  2. additionwas added dropwise
  3. customAfter the completion of the reaction
  4. customthe precipitate was removed by filtration
  5. washthe filtrate was washed with 1 normal hydrochloric acid and further with water
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customAfter the removal of magnesium sulfate
  8. filtrationby filtration
  9. distillationthe solvent was distilled off
  10. customthe residue as it is was used for the following reaction

Sources & evidence

ORD record
ord-b586771cbf49469d9db8d80580d2ac65
Source dataset
uspto-grants-1993_05
Patent number
US05211879

Reaction notes

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