Sodium Iodide → 1-(5-Hydroxy-3-oxapentyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

HRID 37050

Reaction equation

HRID 37050 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][OH:52]>CN(C)C=O>[OH: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 123612-(Chloroethoxy)ethanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

Product 1

HCID 194385451-(5-Hydroxy-3-oxapentyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4,7,10-Tetraazacyclododecane-4,7,10-triacetic acid tri-t-butyl-ester (515 mg, 1 mmol) was dissolved in dimethylformamide (3 ml). Sodium iodide (15 mg, 0.1 mmol), triethylamine (233 mg, 2.5 mmol) and 2(2-chloroethoxy) ethanol (313 mg, 3.5 mmol) were added to the stirred mixture at ambient temperature. The mixture was stirred for 18 hours at ambient temperature. The temperature was then raised to 100° C. and kept there for 1 hour. The solvent was then evaporated and the residue dissolved in a mixture of dichloromethane (4.5 ml) and trifluoroacetic acid (4.5 ml). The mixture was stirred for 2 hours at ambient temperature and the solvent was then evaporated. The residue was dissolved in water (8 ml), and this aqueous solution was washed with ether (6×4 ml). The aqueous solution was acidified and the title compound was isolated as a hygroscopic white powder after evaporation of the water. Yield 325 mg (75%), FAB MS: 435(M+1 ). The structure was confirmed by 1HNMR and 13C NMR.

Workup

  1. temperatureThe temperature was then raised to 100° C.
  2. waitkept there for 1 hour
  3. customThe solvent was then evaporated
  4. dissolutionthe residue dissolved in a mixture of dichloromethane (4.5 ml) and trifluoroacetic acid (4.5 ml)
  5. stirringThe mixture was stirred for 2 hours at ambient temperature
  6. customthe solvent was then evaporated
  7. dissolutionThe residue was dissolved in water (8 ml)
  8. washthis aqueous solution was washed with ether (6×4 ml)

Sources & evidence

ORD record
ord-a09a9c54bb3348709006ef40b418f2b8
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Linked notes

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