Hydrochloric Acid → Dihydroartemisinic acid

HRID 618608

Reaction equation

HRID 618608 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>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10922465Artemisinic Acid

Product 1

HCID 11020893Dihydroartemisinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A process as claimed in step (x) of claim 1, wherein reduction in step (x) comprises (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.

Workup

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

Sources & evidence

ORD record
ord-afead0b5bfee482e863fbb212dd1b31e
Source dataset
uspto-grants-1999_09
Patent number
US05955084

Linked notes

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