Potassium Hydroxide → HCID 57192709, Verbindung

HRID 362742

Reaktionsgleichung

Reaktionsgleichung von HRID 362742
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2]1.[C:21]([CH2:24][N:25]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32][N:31]([CH2:37][C:38]([OH:40])=[O:39])[CH2:30][CH2:29][N:28]([CH2:41][C:42]([OH:44])=[O:43])[CH2:27][CH2:26]1)([OH:23])=[O:22].[OH-].[K+]>O1CCOCC1.O>[OH:1][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:2][N:34]1[CH2:35][CH2:36][N:25]([CH2:24][C:21]([OH:23])=[O:22])[CH2:26][CH2:27][N:28]([CH2:41][C:42]([OH:44])=[O:43])[CH2:29][CH2:30][N:31]([CH2:37][C:38]([OH:40])=[O:39])[CH2:32][CH2:33]1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 11219625HCID 11219625, Verbindung

Produkt 1

HCID 57192709HCID 57192709, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

28.73 g (103.92 mmol) of 1,2-epoxy-11-benzyloxyundecane and 10 g (28.86 mmol) of 1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane (=DO3A) are dissolved in a mixture of 50 ml of dioxane/80 ml of water and the pH is brought to pH 10 with 6N potassium hydroxide solution. It is stirred for 24 hours at 70° C. It is evaporated to dryness, the residue is taken up with 200 ml of water/50 ml of methanol and extracted twice with 100 ml of tert-butyl methyl ether. The aqueous solution is adjusted to pH 3 with 5N hydrochloric acid and evaporated to dryness. The residue is boiled out (extracted) with 200 ml of methanol/80 ml of methylene chloride. It is cooled in an ice bath and filtered off from precipitated potassium chloride. The filtrate is concentrated by evaporation in a vacuum, the residue is dissolved in 45 ml of water/20 ml of ethanol and then added to a column of poly-(4-vinylpyridine). The product is eluted with a solution of ethanol/water 1:3. After concentration by evaporation in a vacuum, the residue is chromatographed on a reversed-phase column (RP 18/mobile solvent=gradient of water/tetrahydrofuran). After concentration by evaporation of the main fraction, 12.22 g (68% of theory) of a strongly hygroscopic, vitreous solid is obtained.

Aufarbeitung

  1. customIt is evaporated to dryness
  2. extractionextracted twice with 100 ml of tert-butyl methyl ether
  3. customevaporated to dryness
  4. extraction(extracted) with 200 ml of methanol/80 ml of methylene chloride
  5. temperatureIt is cooled in an ice bath
  6. filtrationfiltered off
  7. customfrom precipitated potassium chloride
  8. concentrationThe filtrate is concentrated by evaporation in a vacuum
  9. dissolutionthe residue is dissolved in 45 ml of water/20 ml of ethanol
  10. additionadded to a column of poly-(4-vinylpyridine)
  11. washThe product is eluted with a solution of ethanol/water 1:3
  12. concentrationAfter concentration
  13. customby evaporation in a vacuum
  14. customthe residue is chromatographed on a reversed-phase column (RP 18/mobile solvent=gradient of water/tetrahydrofuran)
  15. concentrationAfter concentration
  16. customby evaporation of the main fraction, 12.22 g (68% of theory) of a strongly hygroscopic, vitreous solid
  17. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-37f3b983045c47ca9549b529f5be6971
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05871709

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