Succinic anhydride → HCID 86631996, compound

HRID 910470Notes

Reaction equation

HRID 910470 reaction equation
[CH3:1][C@H:2]1[C@:10]2([OH:24])[C@H:11]3[C@:16]([OH:22])([CH2:17][C:18]([CH2:20][OH:21])=[CH:19][C@H:9]2[C@@H:5]2[C:6]([CH3:8])([CH3:7])[C@:4]2([O:25][C:26]([CH3:28])=[O:27])[CH2:3]1)[C:14](=[O:15])[C:13]([CH3:23])=[CH:12]3.[C:29]1(=[O:35])[O:34][C:32](=[O:33])[CH2:31][CH2:30]1.CN(C1C=CC=CN=1)C>ClCCl>[CH3:1][C@H:2]1[C@:10]2([OH:24])[C@H:11]3[C@:16]([OH:22])([CH2:17][C:18]([CH2:20][OH:21])=[CH:19][C@H:9]2[C@@H:5]2[C:6]([CH3:7])([CH3:8])[C@:4]2([O:25][C:26]([CH3:28])=[O:27])[CH2:3]1)[C:14](=[O:15])[C:13]([CH3:23])=[CH:12]3.[C:29]([O-:34])(=[O:35])[CH2:30][CH2:31][C:32]([O-:15])=[O:33]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 45421760857-08-1

Product 1

HCID 86631996HCID 86631996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prostratin (1390 mg, 1 mmol) and succinic anhydride (120 mg, 1.2 mmol) were dissolved in dichloromethane (20 ml). DMAP (dimethylaminopyridine) at 50 mg was added under stirring and then stirred at room temperature for overnight. The solvent was evaporated and the residue subjected to chromatography on silica gel column (50 mg) with gradient of petroleum ether (60-90° C.) and acetone as eluent to give a fraction of pure prostratin succinate (Scheme (1), product 1) and another fraction containing a mixture of prostratin and prostratin succinate.

Workup

  1. stirringstirred at room temperature for overnight
  2. customThe solvent was evaporated
  3. customsubjected to chromatography on silica gel column (50 mg) with gradient of petroleum ether (60-90° C.) and acetone as eluent

Sources & evidence

ORD record
ord-3d8d2ec0faff42e695d38ac9c1c31cf7
Source dataset
uspto-grants-2011_09
Patent number
US08022103B2

Reaction notes

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