Potassium Hydroxide → HCID 9804183, compound

HRID 2294751Notes

Reaction equation

HRID 2294751 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.[C:8]([CH2:11][N:12]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19][N:18]([CH2:24][C:25]([OH:27])=[O:26])[CH2:17][CH2:16][N:15]([CH2:28][C:29]([OH:31])=[O:30])[CH2:14][CH2:13]1)([OH:10])=[O:9].[OH-].[K+]>O1CCOCC1.O>[OH:5][CH:3]([C:2]([F:7])([F:6])[F:1])[CH2:4][N:21]1[CH2:22][CH2:23][N:12]([CH2:11][C:8]([OH:10])=[O:9])[CH2:13][CH2:14][N:15]([CH2:28][C:29]([OH:31])=[O:30])[CH2:16][CH2:17][N:18]([CH2:24][C:25]([OH:27])=[O:26])[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 5207692-(Trifluoromethyl)oxirane

Product 1

HCID 9804183HCID 9804183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

12.94 g (115.44 mmol) of (1,1,1-trifluoro-2,3-epoxypropane) 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 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, 10.81 g (68% 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, 10.81 g (68% of theory) of a strongly hygroscopic, vitreous solid
  16. customis obtained

Sources & evidence

ORD record
ord-953fd3fbd46b4e31a0a64b68e99a08c3
Source dataset
uspto-grants-1997_11
Patent number
US05690909

Reaction notes

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