Hydrogen Peroxide → 10-Deacetyltaxol

HRID 1780215Notes

Reaction equation

HRID 1780215 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].C([O-])(O)=O.[Na+].OO>C1COCC1>[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:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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: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]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1844927-Epi-Taxol2×HCID 516892Sodium Bicarbonate3×

Product 1

HCID 15583110-Deacetyltaxol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 7-epi-taxol with NaHCO3 : 10 mg (0.01 mmol) of 7-epi-taxol with NaHCO3 in 0.3 ml of THF were introduced into a 4 ml vial equipped with a magnetic stir bar. 0.5 ml of 30% H2O2 was added followed by 100 mg NaHCO3 and the mixture was then stirred at room temperature overnight. The mixture was then extracted with methylene chloride/water (50:50 by volume). The organic phase was collected and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure to obtain a crude product 7-epi-10-deacetyl taxol, that was subsequently purified. Following a 48 hour reaction 25.4% chromo. purity of starting material and 48.3% chrom. purity of 7-epi-10-deacetyl taxol resulted.

Workup

  1. customvial equipped with a magnetic stir bar
  2. extractionThe mixture was then extracted with methylene chloride/water (50:50 by volume)
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-64a5203e848a48ebb43c04512857bae9
Source dataset
uspto-grants-1997_05
Patent number
US05629433

Reaction notes

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