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

HRID 1614518

Reaction equation

HRID 1614518 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][CH2:49][OH:50]>CN(C)C=O>[OH:50][CH2:49][CH2:48][CH2:47][N:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:5])=[O:36])[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 123133-Chloro-1-propanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

Product 1

HCID 194385111-(3-Hydroxy-propyl)-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 (360 mg, 0.70 mmol) (Example 22(a)) was dissolved in dimethylformamide (2.1 ml). Sodium iodide (15 mg, 1 mmol), triethylamine (142 mg, 1.4 mmol) and 3-chloro-1 propanol (132 mg, 1.4 mmol) were added to the stirred mixture at ambient temperature. The mixture was stirred for 3 hours at ambient temperature, the temperature was then raised to 100° C. and kept there for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane (3 ml) and washed with water (1 ml). Trifluoroacetic acid (2 ml) was added to the dichloromethane solution and the mixture was stirred at ambient temperature for 1 hour. The solvents were evaporated and the residue dissolved in water (6 ml). The aqueous solution was washed with ether (6×3 ml). The aqueous solution was acidified, the water was evaporated, and the title compound was isolated as a hygroscopic white powder. Yield 192 mg (68%), FAB MS: 405(M+1). The structure was confirmed by 1HNMR and 13CNMR

Workup

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

Sources & evidence

ORD record
ord-646e2e55d02340b1bbb1f7fe1644cfde
Source dataset
uspto-grants-1993_03
Patent number
US05198208

Linked notes

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