Sodium Iodide → HCID 178453594, compound

HRID 1456347Notes

Reaction equation

HRID 1456347 reaction equation
[I-:1].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18]OS(C)(=O)=O)[CH2:14][CH2:13]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([O:7][C:8]([NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][I:1])[CH2:14][CH2:13]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 178453632HCID 178453632, compound

Product 1

HCID 178453594HCID 178453594, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 130 ml of anhydrous acetone was dissolved 13.24.g of trans-N-t-butoxycarbonyl-4-methanesulfonyloxymethylcyclohexylmethylamine, and 12.32 g of sodium iodide was added thereto, and the resulting mixture was heated under reflux for 3 hours and 45 minutes. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed successively with an aqueous sodium thiosulfate solution and an aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=4/1) to obtain a pale yellow crystalline solid. The crystalline solid was recrystallized from hexane to obtain 13.67 g of the desired compound as a colorless crystalline solid.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 3 hours and 45 minutes
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe resulting solution was washed successively with an aqueous sodium thiosulfate solution
  7. dry with materialan aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=4/1)
  10. customto obtain a pale yellow crystalline solid
  11. customThe crystalline solid was recrystallized from hexane

Sources & evidence

ORD record
ord-8064ac6237be47e9af96ea778112479b
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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