Potassium Hydroxide → HCID 15017858, compound

HRID 1288634Notes

Reaction equation

HRID 1288634 reaction equation
[CH2:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:2]1[O:4][CH2:3]1.[C:10]([CH2:13][N:14]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21][N:20]([CH2:26][C:27]([OH:29])=[O:28])[CH2:19][CH2:18][N:17]([CH2:30][C:31]([OH:33])=[O:32])[CH2:16][CH2:15]1)([OH:12])=[O:11].[OH-].[K+]>O1CCOCC1.O>[OH:4][CH:2]([CH2:1][O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:3][N:23]1[CH2:24][CH2:25][N:14]([CH2:13][C:10]([OH:12])=[O:11])[CH2:15][CH2:16][N:17]([CH2:30][C:31]([OH:33])=[O:32])[CH2:18][CH2:19][N:20]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 243142-((1,1-Dimethylethoxy)methyl)oxiraneHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 15017858HCID 15017858, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

11.27 g (86.58 mmol) of glycidyl-tert-butyl ether and 10 g (28.86 mmol) of 1,4,7-tris-carboxymethyl-1,4,7,10-tetraazacyclododecane are dissolved in a mixture of 50 ml of dioxane/80 ml of water, and the pH is brought to 10 with 6 N potassium hydroxide solution. It is stirred for 24 hours at 70° C. It is evaporated to dryness, the residue is taken up with 300 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 1 with 5 N 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 precipitated potassium chloride is filtered out. The filtrate is concentrated by evaporation in a vacuum, the residue is dissolved in 45 ml of water/20 ml of ethanol and then put on 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, 10.38 g (71% of theory) of a strongly hygroscopic, vitreous solid is obtained.

Workup

  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. customprecipitated potassium chloride
  7. filtrationis filtered out
  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. washThe product is eluted with a solution of ethanol/water 1:3
  11. concentrationAfter concentration
  12. customby evaporation in a vacuum
  13. customthe residue is chromatographed on a reversed-phase column (RP 18/mobile solvent =gradient of water/tetrahydrofuran)
  14. concentrationAfter concentration
  15. customby evaporation of the main fraction, 10.38 g (71% of theory) of a strongly hygroscopic, vitreous solid
  16. customis obtained

Sources & evidence

ORD record
ord-4829568d8adb4b4b92574ae20dd14bae
Source dataset
uspto-grants-1998_05
Patent number
US05747000

Reaction notes

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