Potassium Hydroxide → HCID 21470464, compound

HRID 2294752Notes

Reaction equation

HRID 2294752 reaction equation
[O:1]1[CH2:4][C:2]1([C:5]([F:8])([F:7])[F:6])[CH3:3].[C:9]([CH2:12][N:13]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:25][C:26]([OH:28])=[O:27])[CH2:18][CH2:17][N:16]([CH2:29][C:30]([OH:32])=[O:31])[CH2:15][CH2:14]1)([OH:11])=[O:10].[OH-].[K+]>O1CCOCC1.O>[OH:1][C:2]([C:5]([F:8])([F:7])[F:6])([CH3:3])[CH2:4][N:22]1[CH2:23][CH2:24][N:13]([CH2:12][C:9]([OH:11])=[O:10])[CH2:14][CH2:15][N:16]([CH2:29][C:30]([OH:32])=[O:31])[CH2:17][CH2:18][N:19]([CH2:25][C:26]([OH:28])=[O:27])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 13620760374-11-8

Product 1

HCID 21470464HCID 21470464, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

10.29 g (86.58 mmol) of 2,3-epoxy-2-trifluoromethylpropane 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 6N potassium hydroxide solution. It is stirred for 24 hours at 70° C. (with exclusion of pressure). 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 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 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, 11.04 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, 11.04 g (71% of theory) of a strongly hygroscopic, vitreous solid
  16. customis obtained

Sources & evidence

ORD record
ord-d8b69635ddcc46da913f02dc85a40177
Source dataset
uspto-grants-1997_11
Patent number
US05690909

Reaction notes

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