(+-)-Methionine → (-)-4'-Demethylepipodophyllotoxin

HRID 613776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613776
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9]C.NC(C(O)=O)CCSC.CS(O)(=O)=O.O>CC(C)=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[C@H:22]3[C:23]([O:25][CH2:26][C@@H:21]3[C@H:20]([OH:27])[C:19]3[CH:18]=[C:17]4[O:28][CH2:29][O:30][C:16]4=[CH:15][C:14]2=3)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[OH:9]

Komponenten

6

Edukt 4

HCID 876(+-)-MethionineHCID 962WaterHCID 6395Methanesulfonic AcidHCID 10607Podophyllotoxin

Produkt 1

HCID 122797(-)-4'-Demethylepipodophyllotoxin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 50 g (0.12 mol) of podophyllotoxin I, prepared in 50 ml of acetone, is added with stirring at ordinary temperature to a mixture consisting of 100 g (0.67 mol) of D,L-methionine, of 500 ml (7.7 mol) of methanesulfonic acid and of 10 ml of water. The temperature rises to approximately 40° C. and stirring is maintained for 2 h with return to ambient temperature. The mixture is then poured onto ice in order to obtain a precipitate which is extracted with ethyl acetate (3×700 ml). The organic phases are washed with an NaHCO3 solution and then separated by settling, dried over Na2SO4, filtered and evaporated under reduced pressure in order to obtain 4'-demethylepipodophyllotoxin, existing in the form of a white solid. 45 g (Yd 94%) are obtained.

Aufarbeitung

  1. additionis added
  2. customrises to approximately 40° C.
  3. stirringstirring
  4. additionThe mixture is then poured onto ice in order
  5. customto obtain a precipitate which
  6. extractionis extracted with ethyl acetate (3×700 ml)
  7. washThe organic phases are washed with an NaHCO3 solution
  8. customseparated
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated under reduced pressure in order

Quellen und Nachweise

ORD-Eintrag
ord-2504db1eb8964f899c4a392884571edf
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008382

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