Water → 10-Deacetyltaxol

HRID 1739448Notes

Reaction equation

HRID 1739448 reaction equation
[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(C)=O)[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].NN.O.CCOCC>C(O)C>[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]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:59])[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]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 9321HydrazineHCID 36314Paclitaxel

Product 1

HCID 15583110-DeacetyltaxolYield 86.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of taxol (0.026 g, 0.030 mmol) and 98% hydrazine (0.035 g, 1.1 mmol) in 95% ethanol (1.0 mL) is stirred at room temperature for 2 hr. The solution is poured into water and ether, the mixture is shaken well, and the layers separated. The aqueous layer is extracted with additional ether. The combined ether extracts are dried over Na2SO4, filtered and concentrated, giving 0.021 g of the title compound: 1H NMR spectrum in CDCl3 is identical to the spectrum reported for 10-deacetyltaxol (Ringel, I.; Horwitz, S. B. J. Pharmacol. Exp. Ther., 1987, 242, 692) and is identical to the spectrum of an authentic sample.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer is extracted with additional ether
  3. dry with materialThe combined ether extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fdd0b7649c4f44acbd6547fdc32c0331
Source dataset
uspto-grants-1999_10
Patent number
US05965739

Reaction notes

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