Water → Dihydroartemisinin ethyl ether

HRID 1699476Notes

Reaction equation

HRID 1699476 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].C1(C)C=CC(S(O)(=O)=O)=CC=1.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

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 456410Npc182939

Product 1

HCID 72416Dihydroartemisinin ethyl ether

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Dihydroartemisinin (50 mg) was dissolved in dry ethanol (3 ml). Add 2 ml of triethylorthoformate and (25 mg) of p-toluenesulphonic acid. The reaction mixture was stirred at room temperature (20° C.) for 30 min. 50 ml of water was added in the reaction mixture The reaction product was extracted by dichloromethane (30 mil×3). The dichloromethane extract was dried over anhydrous sodium sulphate and evaporation of solvent under vacuum at 40° C. and yielded the arteether (52 mg).

Workup

  1. extractionwas extracted by dichloromethane (30 mil×3)
  2. extractionThe dichloromethane extract
  3. dry with materialwas dried over anhydrous sodium sulphate and evaporation of solvent under vacuum at 40° C.

Sources & evidence

ORD record
ord-3ef54ade24794d0790ede2b239585204
Source dataset
uspto-grants-2002_02
Patent number
US06346631B1

Reaction notes

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