Cyclohexane → C43H53NO14.3H2O

HRID 2360752Notes

Reaction equation

HRID 2360752 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:39])[C@@H:24]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:40])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:58])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:41][C:42]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:43])[C@:11]2([O:52][C:53]([CH3:55])=[O:54])[CH2:50][O:51][C@@H:10]2[CH2:9][C@@H:8]1[OH:56])=[O:6].C1CCCCC1.O.C(OCC)(=[O:68])C.S([O-])([O-])(=O)=[O:73].[Al+3].[K+].S([O-])([O-])(=O)=[O:80]>C(O)C>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:39])[C@@H:24]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:18][C@@:14]2([OH:40])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:58])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:41][C:42]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:43])[C@:11]2([O:52][C:53]([CH3:55])=[O:54])[CH2:50][O:51][C@@H:10]2[CH2:9][C@@H:8]1[OH:56])=[O:6].[OH2:68].[OH2:73].[OH2:80]

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 24856Potassium AlumHCID 148124DocetaxelHCID 22728543Water ethylacetate

Product 1

HCID 24721032C43H53NO14.3H2OYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
7.5 °C

Procedure

Crude docetaxel (1.0 g) was dissolved in a mixture of ethanol:cyclohexane:demineralised water:ethyl acetate (20:2:10:0.8) containing 0.02 g potassium aluminum sulfate at 25-30° C. under constant stirring. The clear biphasic reaction was then concentrated to 20 ml and cooled to 5-10° C. The precipitated solid was stirred for 25-30 minutes at 5-10° C., then filtered, washed with demineralised water (1 ml) and dried under vacuum under a humid atmosphere (until the moisture content was between 5-7% by Karl Fischer method) to afford Docetaxel trihydrate in 70-90% yield.

Workup

  1. customThe clear biphasic reaction
  2. concentrationwas then concentrated to 20 ml
  3. filtrationfiltered
  4. washwashed with demineralised water (1 ml)
  5. customdried under vacuum under a humid atmosphere (until the moisture content

Sources & evidence

ORD record
ord-06bbd63004de4f70b793d3204dbf0ae3
Source dataset
uspto-grants-2014_04
Patent number
US08686165B2

Reaction notes

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