Succinic anhydride → Paclitaxel Succinate

HRID 265689

Reaktionsgleichung

Reaktionsgleichung von HRID 265689
[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[C:63]1(=[O:69])[O:68][C:66](=[O:67])[CH2:65][CH2:64]1>N1C=CC=CC=1>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([O:40][C:63]([CH2:64][CH2:65][C:66]([OH:68])=[O:67])=[O:69])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6]

Komponenten

4

Edukt 2

HCID 7922Succinic anhydrideHCID 36314Paclitaxel

Produkt 1

HCID 25024567Paclitaxel Succinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Taxol (0.5 g, 0.59 mmol) and succinic anhydride (0.90 g, 7.6 mmol) in 12 ml of pyridine were allowed to react for 3 hours at room temperature after which the mixture was evaporated to dryness in vacuo. The residue was treated with 20 ml of water, stirred for 20 min and then filtered. The precipitate was dissolved in acetone, water slowly added, and the fine crystals of 8 were collected; yield (75-85%).

Aufarbeitung

  1. customto react for 3 hours at room temperature after which the mixture
  2. customwas evaporated to dryness in vacuo
  3. additionThe residue was treated with 20 ml of water
  4. filtrationfiltered
  5. dissolutionThe precipitate was dissolved in acetone
  6. additionwater slowly added
  7. customthe fine crystals of 8 were collected
  8. customyield (75-85%)

Quellen und Nachweise

ORD-Eintrag
ord-f09a019badf44e7dbdde6c69d295f43a
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648506

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