Reaktion #449373

Reaktionsgleichung

NaOH

6,9-dichloro-2-methoxyacridine

quinacrine

1,4-diaminobutane

→

( 29 )

Aminoacridine

Lösungsmittel

phenol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ether
2. 2
   ExtraktionThe ether extract
3. 3
   Waschenis washed with 1M NaHCO3
4. 4
   TrocknenH2O, and dried over MgSO4
5. 5
   SonstigeThe crude product is recrystallized from H2O-alcohol
6. 6
   SonstigeThe phthaloyl protecting group is removed

Vorschrift

A diamine side chain is first synthesized in a manner analogous to the side chain of quinacrine. Specifically, mono-phthaloyl protected 1,4-diaminobutane (27) is reacted with 6,9-dichloro-2-methoxyacridine (28) in phenol (J. Am. Chem. Soc. 66:1921-1924, 1944). The reaction mixture is then poured into an excess of 2N NaOH and extracted with ether. The ether extract is washed with 1M NaHCO3, then H2O, and dried over MgSO4. The crude product is recrystallized from H2O-alcohol. The phthaloyl protecting group is removed using anhydrous hydrazine in MeOH (Bioconjugate Chem. 2:435-440, 1991) to yield the aminoacridine, (29). Aminoacridine (29) is then conjugated with vitamin B12 monocarboxylic acid (2, 3, 4) to yield a cyanocobalamin-acridine conjugate (30).

Quelle