Hydrochloric Acid → HCID 21192220, compound

HRID 1067174Notes

Reaction equation

HRID 1067174 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[CH2:42][CH:28]1[CH2:29][NH:30][C:31](=[O:41])[C:32]1[C:33](=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:34](N)=[O:35].Cl>O.O1CCOCC1>[C:34]([C:33]1[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=1[C:31](=[O:41])[NH:30][CH2:29][CH:28]([OH:27])[CH2:42][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:25])=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 21192206HCID 21192206, compound

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 adjusted to 13 with 5 N sodium hydroxide solution. Then, a solution of 38.12 g (187.6 mmol) of N(2,3-epoxypropyl)-phthalamide in 100 ml of dioxane is instilled within one hour, stirred for 24 hours at 50° C. and the pH is kept at 13 by adding 5 N sodium hydroxide solution. The solution is adjusted to pH 2 with 10% hydrochloric acid and evaporated to dryness 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 the residue is given a final purification by chromatography on RP-18 (LiChroPrep®/mobile solvent: gradient of tetrahydrofuran/methanol/water). After concentration by evaporation of the main fractions, 63.57 g (71% of theory) of an amorphous solid is obtained.

Workup

  1. customevaporated to dryness 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. custompurification by chromatography on RP-18 (LiChroPrep®/mobile solvent: gradient of tetrahydrofuran/methanol/water)
  6. concentrationAfter concentration
  7. customby evaporation of the main fractions, 63.57 g (71% of theory) of an amorphous solid
  8. customis obtained

Sources & evidence

ORD record
ord-31af1e2ca9024131b18bcbb4506d9ae4
Source dataset
uspto-grants-2001_06
Patent number
US06248306B1

Reaction notes

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