Succinic anhydride → HCID 86631996, compound

HRID 1971638Notes

Reaction equation

HRID 1971638 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-7f02a4eecc364646950c4c9efdfc7117
Source dataset
uspto-grants-2013_04
Patent number
US08431612B2

Reaction notes

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