Sodium Iodide → HCID 19438504, compound

HRID 1733785Notes

Reaction equation

HRID 1733785 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH2:16][CH2:15][N:14]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(C)(C)C.[I-].[Na+].C(N(CC)CC)C.Cl[CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][OH:55]>CN(C)C=O>[OH:55][CH2:54][CH2:53][O:52][CH2:51][CH2:50][O:49][CH2:48][CH2:47][N:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:36])=[O:5])[CH2:19][CH2:18][N:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][CH2:15][N:14]([CH2:28][C:29]([OH:31])=[O:30])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 788712-(2-(2-Chloroethoxy)ethoxy)ethanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

Product 1

HCID 19438504HCID 19438504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4,7,10-Tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl ester (129 mg, 0.25 mmol) (Example 22(a)) was dissolved in dimethylformamide (1 ml). Sodium iodide (7.5 mg, 0.5 mmol) , triethylamine (76 mg, 0.75 mmol) and 2-[2-(2-chloroethoxy)-ethoxy]ethanol (85 mg, 0.5 mmol) were added to the stirred mixture at ambient temperature. The mixture was stirred at ambient temperature for 90 minutes, the temperature was then raised to 100° C. and kept there for 1 hour. The solvent was evaporated, and the residue was dissolved in dichloromethane (2 ml) and washed with water (1 ml). Trifluoroacetic acid (2 ml) was added to the organic phase and the mixture was stirred at ambient temperature for 1 hour. The solvents were evaporated and the residue dissolved in water (4 ml). The aqueous solution was acidified, the water was evaporated and the title compound was isolated as a hygroscopic white powder. Yield 77 mg (64%). The structure was confirmed by 1HNMR and 13CNMR.

Workup

  1. temperaturethe temperature was then raised to 100° C.
  2. waitkept there for 1 hour
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane (2 ml)
  5. washwashed with water (1 ml)
  6. additionTrifluoroacetic acid (2 ml) was added to the organic phase
  7. stirringthe mixture was stirred at ambient temperature for 1 hour
  8. customThe solvents were evaporated
  9. dissolutionthe residue dissolved in water (4 ml)
  10. customthe water was evaporated

Sources & evidence

ORD record
ord-76758d6dffbc4a14a836cd90f48bd9ba
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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