Hydrogen Peroxide → HCID 10079106, compound

HRID 748604Notes

Reaction equation

HRID 748604 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].OO.C(=O)(O)[O-].[Na+].ClCCl.O>O1CCCC1>[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])[CH: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

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 36314PaclitaxelHCID 516892Sodium BicarbonateHCID 21908982Water methylene chloride

Product 1

HCID 10079106HCID 10079106, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of paclitaxel (1.0 g, 1.17 mmol) in tetrahydrofuran (20 mL) was added hydrogen peroxide (30%, 20 mL) followed by sodium bicarbonate (1.92 g, 22.85 mmol). After stirring at room temperature for 18 hrs, the mixture was treated with dichloromethane/water (1:1(v/v), 100 mL). The organic phase was washed with water (2×30 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum. The residue was purified by silica gel flash chromatography eluting with 3% methanol/dichloromethane (v/v) to yield 10-deacetylpaclitaxel (890 mg, 93% yield) as a white powder.

Workup

  1. washThe organic phase was washed with water (2×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel flash chromatography
  5. washeluting with 3% methanol/dichloromethane (v/v)

Sources & evidence

ORD record
ord-b6eb7194359242eea048890487ecd746
Source dataset
uspto-grants-2008_07
Patent number
US07399860B2

Reaction notes

Loading…