Diethyl Ether → Clopidogrel Besylate

HRID 555967Notes

Reaction equation

HRID 555967 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>CO>[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 7371Benzenesulfonic AcidHCID 60606Clopidogrel

Product 1

HCID 9847991Clopidogrel Besylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Clopidogrel base was dissolved in methanol. Benzene sulphonic acid was added to the solution at 20° C. The reaction mixture was heated to reflux temperature for 2 hrs. The solution was cooled to room temperature and was added drop-wise to diethyl ether. The suspension was stirred at RT. The solid was filtered and dried in a vacuum oven to give Clopidogrel besylate, similar to that obtained above.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 hrs
  3. filtrationThe solid was filtered
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-18d733889085409893887a2bfdb27e0a
Source dataset
uspto-grants-2011_11
Patent number
US08053579B2

Reaction notes

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