Diethylenetriaminepentaacetic acid → Diethylenetriaminepentaacetic acid

HRID 1252017Notes

Reaction equation

HRID 1252017 reaction equation
NN.[CH2:3]([N:14]([CH2:26][C:27]([OH:29])=[O:28])[CH2:15][CH2:16][N:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][C:19]([OH:21])=[O:20])[CH2:4][N:5]([CH2:10][C:11]([OH:13])=[O:12])[CH2:6][C:7]([OH:9])=[O:8]>CN(C)C=O.CC#N.CN(C)C=O>[CH2:15]([N:14]([CH2:26][C:27]([OH:29])=[O:28])[CH2:3][CH2:4][N:5]([CH2:6][C:7]([OH:9])=[O:8])[CH2:10][C:11]([OH:13])=[O:12])[CH2:16][N:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][C:19]([OH:21])=[O:20].[CH2:15]([N:14]([CH2:26][C:27]([OH:29])=[O:28])[CH2:3][CH2:4][N:5]([CH2:6][C:7]([O-:9])=[O:8])[CH2:10][C:11]([O-:13])=[O:12])[CH2:16][N:17]([CH2:22][C:23]([O-:25])=[O:24])[CH2:18][C:19]([O-:21])=[O:20]

Participants

6

Reactant 2

HCID 3053Diethylenetriaminepentaacetic acidHCID 9321Hydrazine

Product 2

HCID 3053Diethylenetriaminepentaacetic acidHCID 6857479HCID 6857479, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

The hydrazide derivative of DTPA (HDTPA) was prepared as follows: 6.3 mmole of anhydrous hydrazine was dissolved in 2 ml dimethylformamide (DMF) and reacted with 2.54 mmole DTPA mixed anhydride in 20 ml CH3CN-DMF (65:35). The heterogeneous mixture was maintained with stirring at 4° C. for 1 hour, and then at room temperature for 1 hour. The reaction mixture was evaporated to dryness under vacuum, and the residue dissolved in ethanol-aqueous ammonia (4:1). The product was then purified by elution through silica gel with ethanol-aqueous ammonia, followed by distilled water. Product-containing fractions were collected, and the pH adjusted to 3.0 using a small aliquot of hydrochloric acid. The solution was filtered and the filtrate lyophilized to yield HDTPA.

Workup

  1. temperatureThe heterogeneous mixture was maintained
  2. waitat room temperature for 1 hour
  3. customThe reaction mixture was evaporated to dryness under vacuum
  4. dissolutionthe residue dissolved in ethanol-aqueous ammonia (4:1)
  5. customThe product was then purified by elution through silica gel with ethanol-aqueous ammonia
  6. distillationby distilled water
  7. customProduct-containing fractions were collected
  8. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-1b1cf3cefba147d28f48609995f74b3b
Source dataset
uspto-grants-1988_05
Patent number
US04741900

Reaction notes

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