Reaktion #2275690

Reaktionsgleichung

KOH

HCl

KOH

5-Acetylamino-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide

boric acid

→

5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide

Ausbeute 19.0%

Lösungsmittel

Water tBuOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated to dryness
2. 2
   SonstigeThe product was purified by C18 column chromatography
3. 3
   Wascheneluting with MeOH/Water

Vorschrift

To a stirred solution of Water/tBuOH (2:1, 8 mL:10 mL) and KOH (0.73 g, 13 mmol, 1.2 eq was added at 40° C. 5-Acetylamino-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide (8.1 g, 11 mmol). To the clear solution was then added boric acid (0.47 g, 8 mmol, 0.7 eq). The mixture was cooled to room temperature and the pH adjusted to pH 12.6-13.0 with KOH. t-Butyl n-(2-oxiranyl-methyl)carbamate (0.996 g, 8 mmol, 0.7 eq) was added, and the pH was measured several times and adjusted to 12.6-13.0. The mixture was stirred over the weekend. An aqueous solution of HCl was then added until pH 4. The reaction mixture was evaporated to dryness. The product was purified by C18 column chromatography eluting with MeOH/Water to give 5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide (2.09 mmol, Yield=19%).

Quelle