Water → HCID 18940746, compound

HRID 356071Notes

Reaction equation

HRID 356071 reaction equation
[C:1]([N:8]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:9][CH2:10][CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[C:30]([N:37]([CH2:40][CH2:41][CH2:42]Br)[CH2:38][CH3:39])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].O>O1CCOCC1>[CH2:38]([N:37]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:40][CH2:41][CH2:42][N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][CH2:9][N:8]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 18940742HCID 18940742, compoundHCID 18940749HCID 18940749, compound2×

Product 1

HCID 18940746HCID 18940746, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1.85 g (5.1 mmol) of N,N'-di-BOC-N-[2-(2-pyridyl)-ethyl]-1,3-propanediamine in 20 ml of dioxane there are added, with stirring, 0.4 g (10 mmol) of sodium hydride dispersion (approximately 60% in oil; Fluka, Buchs, Switzerland) and, after 20 minutes, a solution of 1.23 ; (6 mmol) of N-BOC-N-ethyl-3-bromo-propylamine in 2 ml of dioxane. The reaction mixture is stirred at 50° C. for 18 hours, a further 0.4 g (10 mmol) of sodium hydride dispersion (approximately 60%) and 1.23 g (6 mmol) of N-BOC-N-ethyl-3-bromo-propylamine are added at 25° C., the mixture is stirred at 50° C. for a further 18 hours and is then coded to room temperature, 50 ml of water are added, and the reaction mixture is extracted with methylene chloride. The methylene chloride extract is dried over sodium sulfate and concentrated by evaporation. and the residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.063 mm using tert-butyl methyl ether. After concentration of the product-containing fractions by evaporation, the title compound is obtained in the form of an oil, Rf value=0.37 (silica gel/tert-butyl methyl ether).

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 18 hours
  2. stirringthe mixture is stirred at 50° C. for a further 18 hours
  3. customis then coded to room temperature
  4. extractionthe reaction mixture is extracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialis dried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customand the residue is purified by flash chromatography on silica gel having a particle size of 0.04-0.063 mm
  9. customAfter concentration of the product-containing fractions by evaporation

Sources & evidence

ORD record
ord-9961d8471781415ab67f76531bbaa7e4
Source dataset
uspto-grants-1998_11
Patent number
US05834486

Reaction notes

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