Benzenesulfonic Acid → Clopidogrel Besylate

HRID 1671498Notes

Reaction equation

HRID 1671498 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>C1COCC1>[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 8028TetrahydrofuranSolvent

Procedure

Clopidogrel base was dissolved in THF. To it, benzene sulfonic acid was added at 20° C., and the reaction mixture was heated to reflux temperature for 2 to 10 hr. The solvent was evaporated to dryness under reduced pressure to obtain Clopidogrel besylate, which on characterization showed to be the amorphous form.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux temperature for 2 to 10 hr
  3. customThe solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8f61e35377a642ed8358008add610e94
Source dataset
uspto-grants-2011_08
Patent number
US07994322B2

Reaction notes

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