Glutaric anhydride → HCID 86585499, compound

HRID 1266958Notes

Reaction equation

HRID 1266958 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:63]1(=[O:70])[O:69][C:67](=[O:68])[CH2:66][CH2:65][CH2:64]1>N1C=CC=CC=1>[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].[C:63]([O-:69])(=[O:70])[CH2:64][CH2:65][CH2:66][C:67]([O-:6])=[O:68]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 36314Paclitaxel

Product 1

HCID 86585499HCID 86585499, compoundYield 170.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Paclitaxel (0.43 g, 0.5 mmol) and glutaric anhydride (0.68 g, 6 mmol) were dissolved in 5 ml of pyridine and stirred at room temperature for 3 hours. In the end of reaction, the solution was evaporated to dryness in vacuo. The residues were treated with 20 ml water with stirring for 20 min and filtered. The precipitates were redissolved in acetone and water was added to produce fine crystals of paclitaxel-glutarate (0.42 g, 86% yields). The analytic result gave [M+H]+=968 Da by ESMs. The paclitaxel-glutarate complex has the following structure:

Workup

  1. customIn the end of reaction
  2. customthe solution was evaporated to dryness in vacuo
  3. additionThe residues were treated with 20 ml water
  4. stirringwith stirring for 20 min
  5. filtrationfiltered
  6. dissolutionThe precipitates were redissolved in acetone
  7. additionwater was added

Sources & evidence

ORD record
ord-8e4857df31d24cb8934fd945befe8914
Source dataset
uspto-grants-2003_04
Patent number
US06552007B2

Reaction notes

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