Potassium Carbonate → HCID 18924360, compound

HRID 1288637Notes

Reaction equation

HRID 1288637 reaction equation
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].Br[CH2:26][CH2:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:30][C:29]([CH3:32])([CH3:31])[O:28][CH2:27][CH2:26][N:14]1[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6][N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 123592832-(2-Bromoethoxy)-2-methylpropane

Product 1

HCID 18924360HCID 18924360, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (14.43 mmol) of 1,4,7-tris-(carboxymethyl)-1,4,7, 10-tetraazacyclododecane is stirred in 75 ml of dimethylformamide for 18 hours with 3.14 g (17.35 mmol) of (2-bromoethyl)-tert-butyl ether and 6.50 g of potassium carbonate at 95° C. It is concentrated by evaporation in a vacuum and the residue is dissolved in 100 ml of water, the pH is adjusted to 2 by adding 12 N hydrochloric acid and the solution is put on a column of 320 ml of cation exchanger IR-120 (H+ form). It is eluted with 2 l of water, which is discarded, then with 2 l of 0.5 N ammonia solution. This solution is concentrated by evaporation in a vacuum, the residue is dissolved in 100 ml of water. With stirring, enough cation exchanger IR-120 is added in portions up to pH 3.5. The solution is filtered and freeze-dried and 4.19 g of the title compound is obtained as white solid with a water content of 6.3%.

Workup

  1. concentrationIt is concentrated by evaporation in a vacuum
  2. dissolutionthe residue is dissolved in 100 ml of water
  3. additionby adding 12 N hydrochloric acid
  4. washIt is eluted with 2 l of water, which
  5. concentrationThis solution is concentrated by evaporation in a vacuum
  6. dissolutionthe residue is dissolved in 100 ml of water
  7. additionenough cation exchanger IR-120 is added in portions up to pH 3.5
  8. filtrationThe solution is filtered
  9. customfreeze-dried

Sources & evidence

ORD record
ord-3a81dd53a92846998e786ccbc502db7c
Source dataset
uspto-grants-1998_05
Patent number
US05747000

Reaction notes

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