Sulfuric Acid → Clopidogrel bisulfate

HRID 1866753Notes

Reaction equation

HRID 1866753 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 bisulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The Clopidogrel free base was then converted into its hydrogen sulfate salt by dissolving in acetone, cooling and mixing with concentrated sulfuric acid to precipitation. The precipitate thus obtained is then isolated by filtration, washed and dried to give Clopidogrel hydrogen sulfate in the form of white crystals whose melting point was 184° C. and optical rotation was +55.1° (c=1.891/CH3OH). But '459 patent did not characterize or suggest any name to this crystals (polymorph) of Clopidogrel hydrogen sulfate.

Workup

  1. temperaturecooling
  2. customThe precipitate thus obtained
  3. customis then isolated by filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-164b4b7846bc4e948862c1be85938d85
Source dataset
uspto-grants-2009_12
Patent number
US07629465B2

Reaction notes

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