Hydrochloric Acid → Dihydroartemisinic acid

HRID 618607

Reaction equation

HRID 618607 reaction equation
[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C:13]([C:15]([OH:17])=[O:16])=[CH2:14])[CH2:4][CH2:3]1.[BH4-].[Na+].Cl>CO.Cl[Ni]Cl>[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10922465Artemisinic Acid

Product 1

HCID 11020893Dihydroartemisinic acid

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

One embodiment of the invention provides a process for the conversion of artemisinic acid into artemisinin employing steps such as reduction and photo oxidation and the reduction is carried out by the following steps comprising (i) dissolving artemisinic acid and NiCl2.6h2O in dry methanol; (ii) adding sodium borohydride to the resultant solution at 0° C. over a 2 hr. period; (iii) neutralising the solution obtained in step (ii) with 5% aqueous HCl solution and (iv) isolating and crystallizing the dihydro artemisinic acid in ethyl acetate to obtain pure dihydro artemisinic acid. However, the step of photo oxidation is carried out by comprising (i) dissolving the dihydroartemisinic acid in the solvent dichloromethane-ethyl acetate; (ii) oxidising the solution obtained in the step (i) in the presence of fluorescent light (40W) daily for two hours upto 8 days; (iii) concentrating the solution obtained in step (ii) and recrystallizing the residue in hexane to isolate artemisinin.

Workup

  1. customisolating
  2. customcrystallizing the dihydro artemisinic acid in ethyl acetate

Sources & evidence

ORD record
ord-551f1f18f3014b5c9f92aaac9631a771
Source dataset
uspto-grants-1999_09
Patent number
US05955084

Linked notes

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