Potassium Iodide → HCID 86588627, compound

HRID 2230221Notes

Reaction equation

HRID 2230221 reaction equation
[Na].[CH3:2][C@@:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][C@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:12][CH:11]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4]1.[I-].[K+].Cl[CH2:26][C:27]([O:29][CH3:30])=[O:28]>CO>[CH3:2][C@@:3]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][C@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:14][CH:15]=2)[C:7](=[O:8])[N:6]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:5](=[O:9])[NH:4]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7295Methyl chloroacetate2×HCID 5360545SodiumHCID 69886777HCID 69886777, compound

Product 1

HCID 86588627HCID 86588627, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

230 mg (10 mmol) of sodium were dissolved in 25 ml of anhydrous methanol under argon. 2.9 g (10 mmol) of 10.2 were added. The mixture was heated to reflux with stirring for 2 hours. 1.66 g (10 mmol) of potassium iodide were then added and a solution of 0.975 ml (10 mmol) of methyl chloroacetate in 1.1 ml of anhydrous methanol was added dropwise in the course of 15 minutes. The mixture was heated to reflux for 4 hours and then allowed to stand at room temperature overnight. A further 0.195 ml (2 mmol) of methyl chloroacetate in 0.22 ml of anhydrous methanol were added and the batch was stirred under reflux for 4 hours. The precipitate was filtered off with suction and the filtrate was concentrated. The residue was dissolved in methylene chloride, insoluble matter was filtered off and the filtrate was chromatographed on silica gel using methylene chloride/ethyl acetate (9:1). 2.56 g (71%) of 10.3 were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 4 hours
  5. waitto stand at room temperature overnight
  6. stirringthe batch was stirred
  7. temperatureunder reflux for 4 hours
  8. filtrationThe precipitate was filtered off with suction
  9. concentrationthe filtrate was concentrated
  10. dissolutionThe residue was dissolved in methylene chloride
  11. filtrationinsoluble matter was filtered off
  12. customthe filtrate was chromatographed on silica gel

Sources & evidence

ORD record
ord-09c14d8ece634999826bae7eea959f41
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

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