Propylene Oxide → 10-(2-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid

HRID 1489343

Reaktionsgleichung

Reaktionsgleichung von HRID 1489343
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].[OH-].[Na+].[CH2:27]1[O:30][CH:28]1[CH3:29]>O>[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][N:14]([CH2:27][CH:28]([OH:30])[CH3:29])[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2]

Komponenten

5

Edukt 3

HCID 6378Propylene OxideHCID 14798Sodium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Produkt 1

HCID 6071510-(2-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 194.0 g (0.56 mol) of 15 in 450 mL of water is added sufficient NaOH to adjust the pH to 12.0 to 12.5 (the temperature is maintained below 30° C. during the addition). Propylene oxide (65 g, 1.12 mols) is added to the basic solution. After 6 hours at ambient temperature the excess propylene oxide and solvent is removed under reduced pressure. The product is precipitated from a minimal amount of methanol to afford 16 in 96% yield.

Aufarbeitung

  1. temperatureis maintained below 30° C. during the addition)
  2. customAfter 6 hours at ambient temperature the excess propylene oxide and solvent is removed under reduced pressure
  3. customThe product is precipitated from a minimal amount of methanol

Quellen und Nachweise

ORD-Eintrag
ord-1dee1909b2904c0d9f99e48353414ef1
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677446

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