1,2-Epoxy-3-methoxypropane → HCID 18924359, compound

HRID 1288633Notes

Reaction equation

HRID 1288633 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:6][CH2:5]1.[C:7]([CH2:10][N:11]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][N:17]([CH2:23][C:24]([OH:26])=[O:25])[CH2:16][CH2:15][N:14]([CH2:27][C:28]([OH:30])=[O:29])[CH2:13][CH2:12]1)([OH:9])=[O:8].[OH-].[K+]>O1CCOCC1.O>[OH:6][CH:4]([CH2:3][O:2][CH3:1])[CH2:5][N:20]1[CH2:21][CH2:22][N:11]([CH2:10][C:7]([OH:9])=[O:8])[CH2:12][CH2:13][N:14]([CH2:27][C:28]([OH:30])=[O:29])[CH2:15][CH2:16][N:17]([CH2:23][C:24]([OH:26])=[O:25])[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 135891,2-Epoxy-3-methoxypropaneHCID 14797Potassium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 18924359HCID 18924359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

7.63 g (86.58 mmol) of glycidyl methyl ether and 10 g (28.86 mmol) of 1,4,7-triscarboxymethyl-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 50° 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 (77% of theory) of a greatly 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 (77% of theory) of a greatly hygroscopic, vitreous solid
  16. customis obtained

Sources & evidence

ORD record
ord-a38a23bfc67943b0ab8dd6e927b402ff
Source dataset
uspto-grants-1998_05
Patent number
US05747000

Reaction notes

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