Sulfuric Acid → Clopidogrel bisulfate

HRID 1884858Notes

Reaction equation

HRID 1884858 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]>CC(C)=O>[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[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[OH:25][S:22]([OH:26])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 60606Clopidogrel

Product 1

HCID 115366Clopidogrel bisulfateYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Clopidogrel base (2.88 g) was dissolved in acetone (23 mL). Aqueous sulfuric acid (20%, 2.56 mL) was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hours. The solution was cooled to room temperature and stirred at this temperature for an additional 2 hours. Then the solvent was evaporated to dryness under reduced pressure to obtain powder (3.08 g, 82%) which characterization data showed to be the amorphous form.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 hours
  3. customThen the solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d0412623ca0146c6b2257f0ba3437ff0
Source dataset
uspto-grants-2004_07
Patent number
US06767913B2

Reaction notes

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