Sulfuric Acid → Clopidogrel bisulfate

HRID 269377Notes

Reaction equation

HRID 269377 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>C(O)(=O)C>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[OH:25][S:22]([OH:26])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 60606Clopidogrel2×

Product 1

HCID 115366Clopidogrel bisulfate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Converting the (S) Clopidogrel camphor sulfonate salt (ISII) to (S) Clopidogrel free base of formula (IS) by the conventional technique. Dissolving the resolved (S) Clopidogrel base (IS) in glacial acetic acid at room temperature; followed by adding an antisolvent containing sulfuric acid to the solution at room temperature. Stirring the reaction mixture for 24 hours at room temperature, filtering and drying the crystals to obtain Form I of Clopidogrel Bisulfate.

Workup

  1. dissolutionDissolving the
  2. customat room temperature
  3. additionby adding an antisolvent
  4. filtrationfiltering
  5. customdrying the crystals

Sources & evidence

ORD record
ord-f72d270f4aa94609bba2c040c8ae09d3
Source dataset
uspto-grants-2008_11
Patent number
US07446200B2

Reaction notes

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