7-Epi-Taxol → HCID 131730074, compound

HRID 1879602Notes

Reaction equation

HRID 1879602 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: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]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[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]>CS(C)=O>[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: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]([O:59][C:60]([CH3:62])=[O:61])[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].[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: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]([O:59][C:60]([CH3:62])=[O:61])[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

3

Reactant 1

HCID 1844927-Epi-Taxol

Product 1

HCID 131730074HCID 131730074, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of paclitaxel/7-epipaclitaxel conjugate was prepared by accurately weighting 350±5 mg of the conjugate in a 10 mL flask and dissolving with dimethylsulfoxide. The solution was diluted to volume with the same solvent. 250±2.5 mg of PPX (Pharmaceutical Grade) were accurately weighed in a 5 mL flask. 0.085 mL of the spiking solution (corresponding to a spiking level of 1.2% w/w) was added in the same flask and diluted to volume with dimethylsulfoxide. The aminolysis reaction was then performed according to the general procedure given in Example 2 and analysed by HPLC. Recovery of 7-epipaclitaxel was 110.7%.

Workup

  1. additionThe solution was diluted to volume with the same solvent
  2. custom250±2.5 mg of PPX (Pharmaceutical Grade) were accurately weighed in a 5 mL flask
  3. customThe aminolysis reaction

Sources & evidence

ORD record
ord-24752ce3137e45f38ef56b1dcbafd680
Source dataset
uspto-grants-2012_11
Patent number
US08318503B2

Reaction notes

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