(RS)-Clopidogrel → 2-chlorophenyl(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (-)-camphorsulfonic acid salt

HRID 434173Notes

Reaction equation

HRID 434173 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1.O.[C:23]12([CH2:33][S:34]([OH:37])(=[O:36])=[O:35])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25]>CC(C)=O>[C:23]12([CH2:33][S:34]([OH:37])(=[O:35])=[O:36])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25].[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1

Participants

4

Reactant 2

HCID 2806(RS)-ClopidogrelHCID 1226536210-Camphorsulfonic acid monohydrate

Product 1

HCID 156143992-chlorophenyl(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (-)-camphorsulfonic acid saltYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

32 g (0.0994 mol) of (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is dissolved in 150 ml of acetone and to the solution 9.95 g (0.0397 mol) of levorotatory 10-camphorsulfonic acid monohydrate is added. The homogenous reaction mixture is allowed to stay at room temperature. After 48 hours a few crystals appear. The mixture is concentrated by evaporation to 50 ml and allowed to stay at room temperature for 24 hours. The resulting crystals are filtered off, washed with acetone and dried. The crystals thus obtained are dissolved again in a very small amount (50 ml) of hot acetone and after cooling the crystals are filtered off, washed with acetone and dried. Thus the title compound is obtained.

Workup

  1. additionis added
  2. customto stay at room temperature
  3. concentrationThe mixture is concentrated by evaporation to 50 ml
  4. waitto stay at room temperature for 24 hours
  5. filtrationThe resulting crystals are filtered off
  6. washwashed with acetone
  7. customdried
  8. customThe crystals thus obtained
  9. temperatureafter cooling the crystals
  10. filtrationare filtered off
  11. washwashed with acetone
  12. customdried

Sources & evidence

ORD record
ord-652092464e534ab2a6b9bac261cefef5
Source dataset
uspto-grants-2003_12
Patent number
US06670486B1

Reaction notes

Loading…