Succinic anhydride → HCID 86615623, compound

HRID 1376719Notes

Reaction equation

HRID 1376719 reaction equation
[CH3:1][CH:2]([C@@:4]12[C@@H:19]([OH:20])[C@:18]34[O:21][C@H:17]3[CH2:16][C@@H:15]3[C@:10]([CH3:26])([CH2:11][CH2:12][C:13]5[C:24](=[O:25])[O:23][CH2:22][C:14]=53)[C@:8]34[O:9][C@H:7]3[C@@H:5]1[O:6]2)[CH3:3].[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28]1.CCCCCC>N1C=CC=CC=1>[CH3:3][CH:2]([C@@:4]12[C@@H:19]([OH:20])[C@:18]34[O:21][C@H:17]3[CH2:16][C@@H:15]3[C@:10]([CH3:26])([CH2:11][CH2:12][C:13]5[C:24](=[O:25])[O:23][CH2:22][C:14]=53)[C@:8]34[O:9][C@H:7]3[C@@H:5]1[O:6]2)[CH3:1].[C:27]([O-:32])(=[O:33])[CH2:28][CH2:29][C:30]([O-:6])=[O:31]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8058HexaneHCID 107985Triptolide

Product 1

HCID 86615623HCID 86615623, compoundYield 136.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triptolide (100 mg) in 10 ml of pyridine was treated with succinic anhydride (150 mg) at room temperature. The reaction was carried out at 85° C. for 30 hours under a nitrogen atmosphere. Hexane (50 ml) was added to the resultant mixture to precipitate a crude product, which was collected by filtration and washed with hexane. The crude product was recrystallized from ether/hexane to yield 90 mg (70%) of triptolide succinate (YM-262), m.p. 111°-113° C.

Workup

  1. customto precipitate a crude product, which
  2. filtrationwas collected by filtration
  3. washwashed with hexane
  4. customThe crude product was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-b9e1ef6bcef34e73be8d6251f0e3297f
Source dataset
uspto-grants-1997_09
Patent number
US05663335

Reaction notes

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