Trifluoroacetic acid → Artemether

HRID 1841576Notes

Reaction equation

HRID 1841576 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+].F[C:24](F)(F)C(O)=O>CO>[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][CH3:24])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 9838675Qing Hau Sau

Product 1

HCID 68911Artemether

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Artemisinin (100 g.) was dissolved in dry methanol (3 ml). Added sodium borohydride (30 mg.) at −5° C. The reaction mixture was stirred for 2 hours. After completion of the reaction, trifluroacetic acid (0.5 ml) was added and the reaction mixture was stirred for 5 hours. The methylation was incompleted and after workup the artemether was purified by prep TLC to yield 46 mg (46%) pure alpha, beta artemether.

Workup

  1. customat −5° C
  2. additionwas added
  3. stirringthe reaction mixture was stirred for 5 hours
  4. customafter workup the artemether was purified by prep TLC

Sources & evidence

ORD record
ord-327bd0ca1ac544a7b5e801d0febf2ffd
Source dataset
uspto-grants-2004_01
Patent number
US06683193B2

Reaction notes

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