Water → Diethylenetriaminepentaacetic acid

HRID 1534086Notes

Reaction equation

HRID 1534086 reaction equation
N1CC[O:4]CC1.[CH2:7]1[N:14]([CH2:15][CH2:16][NH+:17]([CH2:28][C:29]([O-:31])=[O:30])[CH2:18][CH2:19][N:20]2[CH2:27][C:25](=[O:26])[O:24][C:22](=[O:23])[CH2:21]2)[CH2:13][C:11](=[O:12])[O:10][C:8]1=[O:9].[OH2:32]>>[CH2:16]([N:17]([CH2:28][C:29]([OH:31])=[O:30])[CH2:18][CH2:19][N:20]([CH2:27][C:25]([OH:26])=[O:4])[CH2:21][C:22]([OH:24])=[O:23])[CH2:15][N:14]([CH2:7][C:8]([OH:10])=[O:9])[CH2:13][C:11]([OH:12])=[O:32]

Participants

4

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 1676040123911-26-4

Product 1

HCID 3053Diethylenetriaminepentaacetic acid

Procedure

To a 2-liter round bottom flask containing morpholine (400 mL, 4.60 mol) was added DTPA dianhydride (71.5 g, 200 mmol) followed by 150 mL of water. The reaction was stirred for 24 hours and concentrated. The crude material was evaporated three times from 400 mL water and then stirred with 1 L of dry ethanol at 50° C. for 18 hours. The suspension was filtered and the solids were purified by ion-exchange chromatography on AGl-X8 (hydroxide form) resin eluting with water followed by 0.2 N acetic acid to afford 53.0 g of DTPA-BMO.

Workup

  1. concentrationconcentrated
  2. customThe crude material was evaporated three times from 400 mL water
  3. stirringstirred with 1 L of dry ethanol at 50° C. for 18 hours
  4. filtrationThe suspension was filtered
  5. customthe solids were purified by ion-exchange chromatography on AGl-X8 (hydroxide form) resin
  6. washeluting with water

Sources & evidence

ORD record
ord-dda112e2f3ce4f509f5ab04d3677feee
Source dataset
uspto-grants-1992_02
Patent number
US05087440

Reaction notes

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