Methanol → Vinblastine

HRID 1647542

Reaktionsgleichung

Reaktionsgleichung von HRID 1647542
[CH3:1][CH2:2][C:3]1[CH2:14][N:12]2[CH2:13][C@@H:5]([CH2:6][C@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:27]=[C:26]4[C@@:28]56[C@@H:39]([N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:53][CH3:54])[C@@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@H:37]([O:47][C:48]([CH3:50])=[O:49])[C@:33]3([CH2:51][CH3:52])[CH:34]=[CH:35][CH2:36][N:31]([C@H:32]53)[CH2:30][CH2:29]6)[C:8]3[NH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[CH2:10][CH2:11]2)[CH:4]=1.C[OH:60]>>[CH3:1][CH2:2][C@@:3]1([OH:60])[CH2:14][N:12]2[CH2:13][C@H:5]([CH2:6][C@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:27]=[C:26]4[C@:28]56[C@@H:32]7[C@:33]([CH2:51][CH3:52])([C@@H:37]([O:47][C:48]([CH3:50])=[O:49])[C@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@@H:39]5[N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:53][CH3:54])[CH:34]=[CH:35][CH2:36][N:31]7[CH2:30][CH2:29]6)[C:8]3[NH:21][C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:9]=3[CH2:10][CH2:11]2)[CH2:4]1

Komponenten

3

Edukt 2

HCID 887Methanol2×HCID 4433243',4'-Anhydrovinblastine

Produkt 1

HCID 13342VinblastineAusbeute 1 %

Versuchsvorschrift

To a 50 ml-reaction vessel were put 10 ml of MeOH, 1.9 mg of 3',4'-anhydrovinblastine (AVLB), and 1 ml of a MeOH solution of FeCl3 (1.2M), and the mixture was stirred for 30 min. under cooling with ice, while air was bubbled. Following addition of 9 mg of NaBH4, the mixture was stirred for additional 30 min. Then, 2 ml of 25% aqueous ammonia and 20 ml of water were added to make the solution basic. The products were extracted 3 times with 30 ml each of ethyl acetate. The extracts were combined and evaporated to dryness under reduced pressure at 40° or less. The resulting sample was analyzed by HPLC under the same condition of AVLB as well as less than 1% yield of vinblastine (VLB) and leurosidine (LEU) were obtained.

Aufarbeitung

  1. customTo a 50 ml-reaction vessel
  2. temperatureunder cooling with ice, while air
  3. customwas bubbled
  4. additionaddition of 9 mg of NaBH4
  5. stirringthe mixture was stirred for additional 30 min
  6. additionThen, 2 ml of 25% aqueous ammonia and 20 ml of water were added
  7. extractionThe products were extracted 3 times with 30 ml each of ethyl acetate
  8. customevaporated to dryness under reduced pressure at 40° or less

Quellen und Nachweise

ORD-Eintrag
ord-a5b2873bbc0f456e89f6fad59cca05eb
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432279

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