Methyl iodide → HCID 53849509, compound

HRID 1382926Notes

Reaction equation

HRID 1382926 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]([C@@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53808165HCID 53808165, compound

Product 1

HCID 53849509HCID 53849509, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.5 g (23 mmol) of (S)-6-[1-(benzyloxy)formamido]heptanoic acid are added to a suspension of 3.05 g of 55% sodium hydride (70 mmol) in 200 ml of dimethylformamide and the mixture is left to react at 40° for 30 minutes. Thereafter, 13 g (90 mmol) of methyl iodide are added dropwise and the reaction mixture is heated to 70° for 1 hour. After evaporation of the solvent 120 ml of 1N agueous sodium hydroxide solution and 120 ml of ethanol are added and the reaction mixture is heated to reflux for 30 minutes. Thereafter, the mixture is evaporated to half, 100 ml of saturated aqueous sodium bicarbonate solution are added and the mixture is extracted with ethyl acetate. The aqueous phase is acidified and extracted with methylene chloride. The organic phase is dried over magnesium sulphate and evaporated. The residue (5 g) is chromatographed on silica gel with a 12:1 mixture of methylene chloride and methanol, whereby there are obtained 3.5 g (52.2%) of (S)-6-[1-(benzyloxy)-N-methylformamido]heptanoic acid, MS: M+ 293.

Workup

  1. waitthe mixture is left
  2. customto react at 40° for 30 minutes
  3. temperaturethe reaction mixture is heated to 70° for 1 hour
  4. customAfter evaporation of the solvent 120 ml of 1N agueous sodium hydroxide solution and 120 ml of ethanol
  5. additionare added
  6. temperaturethe reaction mixture is heated
  7. temperatureto reflux for 30 minutes
  8. customThereafter, the mixture is evaporated to half, 100 ml of saturated aqueous sodium bicarbonate solution
  9. additionare added
  10. extractionthe mixture is extracted with ethyl acetate
  11. extractionextracted with methylene chloride
  12. dry with materialThe organic phase is dried over magnesium sulphate
  13. customevaporated
  14. customThe residue (5 g) is chromatographed on silica gel with a 12:1 mixture of methylene chloride and methanol, whereby there

Sources & evidence

ORD record
ord-0ec4692589a040b9ae1b76fc12c3f0dd
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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