Iodoethane → HCID 53671959, compound

HRID 1288630Notes

Reaction equation

HRID 1288630 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH:7]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:35](I)[CH3:36].C(=O)(O)[O-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:32])[CH:7]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:35][CH3:36])=[CH:29][CH:30]=1)[N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 53668792HCID 53668792, compound

Product 1

HCID 53671959HCID 53671959, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

13.2 g (30 mmol) of N-benzyl-2-(4-hydroxybenzyl)-3-azaglutaric acid-di-tert-butyl ester (Example b) is dissolved in 50 ml of anhydrous N,N-dimethylformamide and mixed at 0° C. under argon with 1.31 g (33 mmol) of sodium hydride dispersion (60% in mineral oil). The batch is allowed to stir for 15 minutes, then 8.05 g (51.7 mmol) of ethyl iodide is added, the reaction temperature is allowed to increase to room temperature and it is stirred for another three hours. For working-up, the batch is taken up in toluene and shaken out several times against aqueous sodium bicarbonate solution. The organic phase is separated, dried on magnesium sulfate, filtered and concentrated by evaporation. The oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine. The product fractions are concentrated by evaporation in a vacuum and dried.

Workup

  1. stirringit is stirred for another three hours
  2. customThe organic phase is separated
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine
  7. concentrationThe product fractions are concentrated by evaporation in a vacuum
  8. customdried

Sources & evidence

ORD record
ord-a227984b76c54b8b8b53c4bf308ad3aa
Source dataset
uspto-grants-1998_05
Patent number
US05746995

Reaction notes

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