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

HRID 1733787

Reaktionsgleichung

Reaktionsgleichung von HRID 1733787
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

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 123133-Chloro-1-propanolHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate

Produkt 1

HCID 194385111-(3-Hydroxy-propyl)-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-631e82bf45fd4358ad5838d39952b72c
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05531978

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