Water → Dihydroartemisinin ethyl ether

HRID 1699475

Reaction equation

HRID 1699475 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

Conditions

Temperature
40 °C

Procedure

Dihydroartemisinin (50 mg) was dissolved in dry ethanol (3 ml) In the reaction mixture ptoluene sulphonic acid (25 mg) and triethylorthoformate (2 ml) was added. After addition reaction mixture was stirred at 40° C. for 15 min. at oil bath. After cooling, 50 ml water was added in the reaction mixture. The reaction product was extracted with dichloromethane (30 ml×3). Total solvent obtained was dried over anhydrous sodium sulphate and evaporate the solvent under reduced pressure at 45° C. The yield of pure arteether obtained was 50 mg. The compound was characterised by IR, Mass, 1H NMR.

Workup

  1. additionwas added
  2. additionAfter addition reaction mixture
  3. temperatureAfter cooling
  4. extractionThe reaction product was extracted with dichloromethane (30 ml×3)
  5. customTotal solvent obtained
  6. dry with materialwas dried over anhydrous sodium sulphate
  7. customevaporate the solvent under reduced pressure at 45° C

Sources & evidence

ORD record
ord-b83677fb7228452cb2cc02b9457830b8
Source dataset
uspto-grants-2002_02
Patent number
US06346631B1

Linked notes

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