Water → Dihydroartemisinin ethyl ether

HRID 1699478Notes

Reaction equation

HRID 1699478 reaction equation
[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:19])[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.[CH2:21](OC(OCC)OCC)[CH3:22].O>C(O)C>[CH3:21][CH2:22][O:19][C@H:7]1[O:8][C@@H:9]2[O:15][C:14]3([CH3:18])[O:16][O:17][C@@:10]42[C@@H:5]([CH2:4][CH2:3][C@@H:2]([CH3:1])[C@@H:11]4[CH2:12][CH2:13]3)[C@H:6]1[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 31214Ethyl orthoformateHCID 456410Npc182939

Product 1

HCID 72416Dihydroartemisinin ethyl ether

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dihydroartemisinin (50 mg) was dissolved in 3 ml dry ethanol with stirring the solution for 10 min. at room temperature and add cation exchange resin (Dowex-50, 50 mg) and triethylorthoformate (4 ml) in the solution. The reaction mixture is stirred for 10 hrs at room temperature (30° C.). Water was added in the reaction mixture and filters the cation exchange resin. The reaction product was extracted by dichloromethane. The organic layer was separated, dried over anhydrous sodium sulphate and evaporated under vacuum to yield pure arteether (50 mg).

Workup

  1. stirringThe reaction mixture is stirred for 10 hrs at room temperature (30° C.)
  2. extractionThe reaction product was extracted by dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-27d23df026d04dff94bd070d683976bf
Source dataset
uspto-grants-2002_02
Patent number
US06346631B1

Reaction notes

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