HCID 54074558, compound → HCID 54292926, compound

HRID 1904177Notes

Reaction equation

HRID 1904177 reaction equation
[C:1]([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])#[N:2]>C(O)(=O)C.[Pt]=O>[NH2:2][CH2:1][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]

Participants

4

Reactant 1

HCID 54074558HCID 54074558, compound

Product 1

HCID 54292926HCID 54292926, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of [((6-cyanohexyl)imino)bis(ethylenenitrilo)]tetraacetic acid (0.85g, 0.0019 mol) in acetic acid (50 ml) was treated with platinum oxide (0.15g) and hydrogenated at 45 psi overnight. The catalyst was removed by filtration through celite and the filter pad was rinsed with water. The solvent was removed under reduced pressure to yield crude product, which was chromatographed on a Bio Rad AG 1×8 ion exchange resin in the formate form. Elution with water gave pure [((7-aminoheptyl)imino)bis(ethylenenitrilo)]tetraacetic acid (0.70g, 82%). The product was one spot on tlc. The proton and carbon nmr spectra were consistent with the assigned structure.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washthe filter pad was rinsed with water
  3. customThe solvent was removed under reduced pressure
  4. customto yield crude product, which
  5. customwas chromatographed on a Bio Rad AG 1×8 ion exchange resin in the formate form
  6. washElution with water

Sources & evidence

ORD record
ord-c6657ebaf2a54cd0899a7db96e2a9e5a
Source dataset
uspto-grants-1989_06
Patent number
US04837003

Reaction notes

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