Hydrochloric Acid → HCID 21192220, compound

HRID 1108658Notes

Reaction equation

HRID 1108658 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-:25].[Na+].[O:27]1[CH2:41][CH:28]1[CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].Cl>O.O1CCOCC1>[C:31]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[C:34](=[O:35])[NH:30][CH2:29][CH:28]([OH:27])[CH2:41][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)([OH:40])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 21192220HCID 21192220, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

50 g (144.3 mmol) of 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane (D03A) is dissolved in 250 ml of water, and the pH is set at 13 with 5N sodium hydroxide solution. Then, a solution of 38.12 g (187.6 mmol) of N(2,3-epoxypropyl)phthalimide (Aldrich) in 100 ml of dioxane is added in drops within one hour, stirred for 24 hours at 50° C., and the pH is kept at 13 by adding 5N sodium hydroxide solution. The solution is set at pH 2 with 10% hydrochloric acid and evaporated to the dry state in a vacuum. The residue is dissolved in some water and purified on an ion-exchange column (Reillex®=poly-(4-vinyl)pyridine (it is eluted with water). The main fractions are concentrated by evaporation in a vacuum, and final purification of the residue is achieved by chromatography on RP-18 (LiChroPrep®/mobile solvent: gradient that consists of tetrahydrofuran/methanol/water). After the main fractions are concentrated by evaporation, 63.57 g (71% of theory) of an amorphous solid is obtained.

Workup

  1. customevaporated to the dry state in a vacuum
  2. dissolutionThe residue is dissolved in some water
  3. custompurified on an ion-exchange column (Reillex®=poly-(4-vinyl)pyridine (it is eluted with water)
  4. concentrationThe main fractions are concentrated by evaporation in a vacuum
  5. customfinal purification of the residue
  6. concentrationAfter the main fractions are concentrated by evaporation, 63.57 g (71% of theory) of an amorphous solid
  7. customis obtained

Sources & evidence

ORD record
ord-27ef0d95530449e5b3eed4d561157bcd
Source dataset
uspto-grants-2000_05
Patent number
US06068831

Reaction notes

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