Reaktion #1463901

ord-b9e1ef6bcef34e73be8d6251f0e3297f

Reaktionsgleichung

CCCCCC
Hexane
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@@H]2O
Triptolide
O=C1CCC(=O)O1
succinic anhydride
→
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@@H]2O.O=C([O-])CCC(=O)[O-]
triptolide succinate
Ausbeute 136.2%

Edukte

—
resultant mixture
CCCCCC
Hexane
CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@H]1C4=C(CC[C@@]13C)C(=O)OC4)[C@@H]2O
Triptolide
O=C1CCC(=O)O1
succinic anhydride

Reagenzien

Keine

Lösungsmittel

c1ccncc1
pyridine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto precipitate a crude product, which
  2. 2
    Filtrationwas collected by filtration
  3. 3
    Waschenwashed with hexane
  4. 4
    SonstigeThe crude product was recrystallized from ether/hexane

Vorschrift

Triptolide (100 mg) in 10 ml of pyridine was treated with succinic anhydride (150 mg) at room temperature. The reaction was carried out at 85° C. for 30 hours under a nitrogen atmosphere. Hexane (50 ml) was added to the resultant mixture to precipitate a crude product, which was collected by filtration and washed with hexane. The crude product was recrystallized from ether/hexane to yield 90 mg (70%) of triptolide succinate (YM-262), m.p. 111°-113° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05663335uspto-grants-1997_09