Toluene → 4-methylbenzenesulfonate;methyl (2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate

HRID 15383Notes

Reaction equation

HRID 15383 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([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1.C1(C)C=CC=CC=1>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[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4].[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)([O-:31])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 60606Clopidogrel

Product 1

HCID 866092744-methylbenzenesulfonate;methyl (2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Clopidogrel base was dissolved in methanol. p-Toluene 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 the methanolic solution was added dropwise to hot toluene. The resulting solution was refluxed for an additional 20 minutes. The solution was cooled to room temperature and was stirred for 24 hrs. The solvent was evaporated under reduced pressure to dryness to obtain Clopidogrel tosylate, similar to that obtained above.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 hrs
  3. temperatureThe resulting solution was refluxed for an additional 20 minutes
  4. temperatureThe solution was cooled to room temperature
  5. customThe solvent was evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-617d84fd13554e14921bcedba6bd96e6
Source dataset
uspto-grants-2010_06
Patent number
US07732608B2

Reaction notes

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