Benzenesulfonic Acid → Clopidogrel Besylate

HRID 15388

Reaction equation

HRID 15388 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].[C:22]1([S:28]([OH:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)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[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH:25]1[CH:26]=[CH:27][C:22]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 60606Clopidogrel

Product 1

HCID 9847991Clopidogrel Besylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
27.5 °C

Procedure

Clopidogrel base was dissolved in diethyl ether at 20-25° C. To this was added benzene sulphonic acid dissolved in diethyl ether. The reaction mixture was stirred at 25-30° C. for 24-30 hrs. The white solid was collected by filtration, washed with diethyl ether, and dried at 50-60° C. in a vacuum oven to obtain Clopidogrel besylate crystalline form.

Workup

  1. filtrationThe white solid was collected by filtration
  2. washwashed with diethyl ether
  3. customdried at 50-60° C. in a vacuum oven

Sources & evidence

ORD record
ord-af1d0da647c244b5a90bdaf4cf6fec21
Source dataset
uspto-grants-2010_06
Patent number
US07732608B2

Linked notes

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