Succinic anhydride → Artesunate

HRID 1839859Notes

Reaction equation

HRID 1839859 reaction equation
[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C:7]([O:9][C@@H:10]4[O:16]3)=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+].[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1.C(N(CC)CC)C>O1CCCC1>[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C@H:7]([O:8][C:23]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:29])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 9838675Qing Hau Sau

Product 1

HCID 6917864ArtesunateYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Artemisinin (500 mg) and cation exchange resin (1 g) are stirred in tetrahydrofuran (10 ml) at room temperature for 5 minutes. Sodium borohydride (250 mg) is added slowly for 10 minutes and the reaction mixture is stirred for about 30 minutes at room temperature (20-35 degree C.). After completion of the reaction succinic anhydride (250 mg) and triethylamine (0.7 ml) are added at room temperature and the reaction mixture is stirred further for 1 hours at room temperature. The resin is filtered. After usual workup and column chromatography of the crude product (710 mg), 480 mg of pure artesunic acid (yield=96% w/w) is obtained.

Workup

  1. additionare added at room temperature
  2. stirringthe reaction mixture is stirred further for 1 hours at room temperature
  3. filtrationThe resin is filtered

Sources & evidence

ORD record
ord-779dfdd75d90484cb0f990b5abed999a
Source dataset
uspto-grants-2004_01
Patent number
US06677463B1

Reaction notes

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