Docetaxel → C43H53NO14.3H2O

HRID 1760062

Reaction equation

HRID 1760062 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]>C(#N)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].[OH2:6].[OH2:6].[OH2:6]

Participants

3

Reactant 1

HCID 148124Docetaxel

Product 1

HCID 24721032C43H53NO14.3H2OYield 338.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Docetaxel (460 gm obtained from step 2b) is dissolved in filtered acetonitrile (13.8 L) at 68° C. under stirring. To this solution purified water (41.4 L) is added slowly and then the mixture is stirred further at 15-20° C. for 3h. The precipitated material is filtered and then dried at 36° C. under 650 mm mercury vacuum for 36h to obtain docetaxel trihydrate (415 gm, C.P. 99.59%, assay 99.2% on dry basis, water content 6.8%).

Workup

  1. customTo this solution purified water (41.4 L)
  2. additionis added slowly
  3. stirringthe mixture is stirred further at 15-20° C. for 3h
  4. filtrationThe precipitated material is filtered
  5. dry with materialdried at 36° C. under 650 mm mercury vacuum for 36h

Sources & evidence

ORD record
ord-23cb435699ed41dfb5a50466d0359c2f
Source dataset
uspto-grants-2005_01
Patent number
US06838569B2

Linked notes

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