Dichloromethane → Acetone cardice

HRID 1290132Notes

Reaction equation

HRID 1290132 reaction equation
[CH3:1][CH:2]1[C:7]([O:10][C:11]([CH3:13])=[O:12])([CH2:8][OH:9])[CH:6]2[CH:14]([O:53][C:54]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[O:55])[C:15]3([OH:52])[C:20]([CH3:22])([CH3:21])[C:19]([CH:23]([O:26][C:27]([CH3:29])=[O:28])[C:24](=[O:25])[C:5]2([CH3:62])[CH:4]([OH:63])[CH2:3]1)=[C:18]([CH3:30])[CH:17]([O:31][C:32]([CH:34]([OH:51])[CH:35]([NH:42][C:43]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:16]3.C(Cl)Cl>CC(C)=O>[C:11](=[O:12])=[O:10].[CH3:6][C:7]([CH3:2])=[O:10].[CH3:1][CH:2]1[C:7]([O:10][C:11]([CH3:13])=[O:12])([CH2:8][OH:9])[CH:6]2[CH:14]([O:53][C:54]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)=[O:55])[C:15]3([OH:52])[C:20]([CH3:21])([CH3:22])[C:19]([CH:23]([O:26][C:27]([CH3:29])=[O:28])[C:24](=[O:25])[C:5]2([CH3:62])[CH:4]([OH:63])[CH2:3]1)=[C:18]([CH3:30])[CH:17]([O:31][C:32]([CH:34]([OH:51])[CH:35]([NH:42][C:43]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:44])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[CH2:16]3

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 24728718HCID 24728718, compound

Product 2

HCID 18522661Acetone cardiceHCID 24728718HCID 24728718, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

No paclitaxol was found in the foreruns of experiments conducted with methylene chloride and acetone as cosolvents at 10 mole %. About half of the paclitaxol (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 paclitaxol (0.0147% with a purification factor of 15) from the silica column.

Workup

  1. customAbout half of the paclitaxol (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-152c35789825441fa93579b53f0d3d0c
Source dataset
uspto-grants-1998_05
Patent number
US05750709

Reaction notes

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