Dimethyl Sulfoxide → Paclitaxel

HRID 1008657Notes

Reaction equation

HRID 1008657 reaction equation
CS(C)=[O:3].[CH3:5][C:6]1[C@@H:22]([O:23][C:24]([C@H:26]([OH:43])[C@@H:27]([NH:34][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:36])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][C@:17]2([OH:44])[C:18]([CH3:20])([CH3:19])[C:7]=1[C@@H:8]([O:62][C:63]([CH3:65])=[O:64])[CH2:9][C@@:10]1([CH3:61])[C@H:15]([C@@H:16]2[O:45][C:46]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:47])[C@:14]2([O:56][C:57]([CH3:59])=[O:58])[CH2:54][O:55][C@@H:13]2[CH2:12][C@@H:11]1[OH:60]>O1CCCC1>[CH3:5][C:6]1[C@@H:22]([O:23][C:24]([C@H:26]([OH:43])[C@@H:27]([NH:34][C:35]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:36])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH2:21][C@:17]2([OH:44])[C:18]([CH3:19])([CH3:20])[C:7]=1[C@@H:8]([O:62][C:63]([CH3:65])=[O:64])[C:9]([C@@:10]1([CH3:61])[C@H:15]([C@@H:16]2[O:45][C:46]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:47])[C@:14]2([O:56][C:57]([CH3:59])=[O:58])[CH2:54][O:55][C@@H:13]2[CH2:12][C@@H:11]1[OH:60])=[O:3]

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 9875915HCID 9875915, compound

Product 1

HCID 36314Paclitaxel

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A coated stent from Example 9 is dipped into a DESMODUR solution (50:50 mixture of dimethylsulfoxide and tetrahydrofuran). The device is then removed and the coating is then partially dried at room temperature for 3 to 5 minutes. The device is then immersed in a beaker of water (room temperature) for 3-5 minutes to cause the polymerization reaction to occur rapidly. An echogenic coating is formed. In addition to 9-deoxotaxol, the following are exemplary compounds that may be used to coat the device: 7-deoxy-9-deoxotaxol and 10-desacetoxy-7-deoxy-9-deoxotaxol.

Workup

  1. customThe device is then removed
  2. customthe coating is then partially dried at room temperature for 3 to 5 minutes
  3. customthe polymerization reaction
  4. customAn echogenic coating is formed

Sources & evidence

ORD record
ord-93cccda84f2e4d168072888755608119
Source dataset
uspto-grants-2011_07
Patent number
USH0002260H1

Reaction notes

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