Succinic anhydride → Artesunate

HRID 1839858Notes

Reaction equation

HRID 1839858 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.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[BH4-].[Na+].[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[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:35]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:41])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 7922Succinic anhydrideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 9838675Qing Hau Sau

Product 1

HCID 6917864Artesunate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Artemisinin (500 mg) and polyhydroxy compound (dextrose, 2 g) are stirred in dioxan (15 ml) for 5 minutes. Sodium borohydride (2.4 gm) is added slowly and the reaction mixture is stirred for 2 hours at room temperature (20-30 degree C.). After completion of the reduction step succinic anhydride (250 mg) and sodium bicarbonate (3.5 g) are added and the reaction mixture is further stirred for 2 hours. After usual workup and purification of impure reaction product (650 mg), 89.6% w/w pure artesunic acid is obtained.

Workup

  1. stirringthe reaction mixture is further stirred for 2 hours
  2. customAfter usual workup and purification of impure reaction product (650 mg)

Sources & evidence

ORD record
ord-69355f58753843b9a01f7d3ff5de6bcd
Source dataset
uspto-grants-2004_01
Patent number
US06677463B1

Reaction notes

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