Dichloromethane → Paclitaxel

HRID 1756285Notes

Reaction equation

HRID 1756285 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: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].C(Cl)Cl>CC(C)=O>[C:21](=[O:22])=[O:20].[CH3:4][C:5]([CH3:7])=[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

5

Reactant 2

HCID 6344DichloromethaneHCID 36314Paclitaxel

Product 2

HCID 36314PaclitaxelHCID 18522661Acetone cardice

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

No taxol was found in the foreruns of experiments conducted with methylene chloride and acetone as cosolvents at 10 mole %. About half of the taxol (0.0242%) with a purification factor of 16 was recovered from the silica column in a methylene chloride cosolvent experiment (TAXC-36C). A SCF CO2 /acetone experiment (TAXC-37C) yielded less taxol (0.0147% with a purification factor of 15) from the silica column.

Workup

  1. customAbout half of the taxol (0.0242%) with a purification factor of 16 was recovered from the silica column in a methylene chloride cosolvent experiment (TAXC-36C)

Sources & evidence

ORD record
ord-f40e78c14fa34bcbb43dc3159ae8bafe
Source dataset
uspto-grants-1995_08
Patent number
US05440055

Reaction notes

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