Sodium Hydroxide → 10-(2,3,4-Trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane

HRID 1271796Notes

Reaction equation

HRID 1271796 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].[OH-].[Na+].CC1(C)[O:32][CH:31]([CH:33]2[O:35][CH2:34]2)[CH2:30][O:29]1>O.O1CCOCC1>[OH:35][CH:33]([CH:31]([OH:32])[CH2:30][OH:29])[CH2:34][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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 131868272,2-Dimethyl-4-(oxiran-2-YL)-1,3-dioxolane

Product 1

HCID 1069484210-(2,3,4-Trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

10.0 g (28.87 mmol) of 1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane (DO3A) is dissolved in 40 ml of water, and the pH is set at 13 with 5N sodium hydroxide solution. A solution of 6.24 g (43.30 mmol) of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylene oxide (DE 3,150,917) in 10 ml of dioxane is added thereto, and the mixture is stirred for 24 hours at room temperature. The mixture is diluted with 60 ml of water and extracted three times with 50 ml of ether. The aqueous phase is brought to pH 2 with 10% strength hydrochloric acid and evaporated. The residue is dissolved in a small amount of water and passed to a cation exchange column (IR 120). After flushing with water, the ligand is eluted with 0.5-normal aqueous ammonia solution.

Workup

  1. extractionextracted three times with 50 ml of ether
  2. customevaporated
  3. dissolutionThe residue is dissolved in a small amount of water
  4. customAfter flushing with water
  5. washthe ligand is eluted with 0.5-normal aqueous ammonia solution

Sources & evidence

ORD record
ord-7f035f6eeabf47279bb710a7d05c25a9
Source dataset
uspto-grants-2007_04
Patent number
US07208139B2

Reaction notes

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