Lithium Hydroxide → HCID 21844866, compound

HRID 618914Notes

Reaction equation

HRID 618914 reaction equation
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Li+].Br[CH:16]([CH:20](Br)[C:21]([OH:23])=[O:22])[C:17]([OH:19])=[O:18]>>[N:1]1([CH:16]([CH:20]([N:1]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:21]([OH:23])=[O:22])[C:17]([OH:19])=[O:18])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 649631,4,7,10-TetraazacyclododecaneHCID 953242,3-Dibromosuccinic acid

Product 1

HCID 21844866HCID 21844866, compoundYield 16.2%

Conditions

Temperature
60 °C

Procedure

To an aqueous solution of 1,4,7,10-tetraazacyclododecane (100 g, 580 mmol) and lithium hydroxide (5.2 g, 216 mmol) was added 2,3-dibromosuccinic acid (15.0 g, 54 mmol). After stirring at 60° C. for 3 days, the solution was cooled to ambient temperature and applied on an AG1-X8 anion exchange column [500 mL (OH-form)], the column was washed with water (1 L) and the product was eluted with 1M CH3COOH. Further purification by cation exhange chromatography on a AG5OW-X8 column [100 mL (H+form)] yielded 4.0 g (16%) of the title product as a white powder. 1H NMR (D2O) δ 2.4-3.0 (m, 32H), 3.2 (2H). 13C NMR (D2O) 40.4, 40.7, 42.9, 44.7, 61.5, 174.0. MS (FAB): m/e 459.3.

Workup

  1. temperaturethe solution was cooled to ambient temperature
  2. washthe column was washed with water (1 L)
  3. washthe product was eluted with 1M CH3COOH
  4. customFurther purification by cation exhange chromatography on a AG5OW-X8 column [100 mL (H+form)]

Sources & evidence

ORD record
ord-450ebaaaa1d54c508a6f03e128863449
Source dataset
uspto-grants-1999_09
Patent number
US05958373

Reaction notes

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