HCID 20038264, compound → HCID 19693325, compound

HRID 1904178Notes

Reaction equation

HRID 1904178 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:21][CH2:22][N:23]([CH2:28][C:29]([OH:31])=[O:30])[CH2:24][C:25]([OH:27])=[O:26])[CH2:10][CH2:11][N:12]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][C:14]([OH:16])=[O:15].C(CON1[C:41](=[O:42])[CH:40]=[CH:39][C:38]1=[O:43])(O)=O>C(=O)(O)[O-].[Na+]>[C:38]1(=[O:43])[N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:21][CH2:22][N:23]([CH2:24][C:25]([OH:27])=[O:26])[CH2:28][C:29]([OH:31])=[O:30])[CH2:10][CH2:11][N:12]([CH2:13][C:14]([OH:16])=[O:15])[CH2:17][C:18]([OH:20])=[O:19])[C:41](=[O:42])[CH:40]=[CH:39]1

Participants

4

Reactant 2

HCID 20038264HCID 20038264, compoundHCID 54292926HCID 54292926, compound

Product 1

HCID 19693325HCID 19693325, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of [((7-aminoheptyl)imino)bis(ethylenenitrilo)]tetraacetic acid (0.72g, 1.6 mmol) in saturated aqueous sodium bicarbonate (15 ml) was cooled in an ice bath and N-carboxymethoxymaleimide (prepared according to Helv. Chim. Acta, 58, 531 [1975]) (0.25 g, 1.6 mmol) was added in one portion. After stirring 20 minutes the ice bath was removed and stirring was continued for 30 minutes. The solution was brought to ph≈6 with 1N HC1 and concentrated under reduced pressure. The residue was chromatographed on a 2×30 cm column of Bio-Rad AG 1×8 ion exchange resin in the formate form (gradient elution, 0-1M formic acid) to provide 0.61 g of slightly impure product. This material was rechromatographed as above to yield pure [((7-maleimidoheptyl)imino)bis(ethylenenitrilo)]tetraacetic acid (0.42g, 50%).

Workup

  1. customwas removed
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on a 2×30 cm column of Bio-Rad AG 1×8 ion exchange resin in the formate form (gradient elution, 0-1M formic acid)
  4. customto provide 0.61 g of slightly impure product
  5. customThis material was rechromatographed as above

Sources & evidence

ORD record
ord-e7c0489f261044f6bff5885d2e001cbf
Source dataset
uspto-grants-1989_06
Patent number
US04837003

Reaction notes

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