Sulfuric Acid → Clopidogrel hydrogen sulfate

HRID 988855Notes

Reaction equation

HRID 988855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].[OH:22][S:23]([OH:26])(=[O:25])=[O:24]>CC(C)=O>[S:23](=[O:24])(=[O:22])([OH:26])[OH:25].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 2806(RS)-Clopidogrel

Product 1

HCID 16757820Clopidogrel hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To 2 g (+)Methyl (2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetate was added 5 mL of acetone and stirred at 25-30° C. The temperature of the reaction mixture was raised from 25 to 65° C. and then kept at 65° C. for 5 min. At temperature 50-52° C. 0.676 g of concentrated H2SO4 was added. The reaction mixture was cooled from 52° C. to 5° C., and additional acetone was added and stirred for 5 min. Later the reaction mixture was stirred at 25-30° C. for 12 hrs, the thick precipitate obtained was filtered, washed with 5 mL of acetone and the residue was dried in a vacuum oven. The yield of titled product obtained was 1.27 g (47%).

Workup

  1. temperatureThe temperature of the reaction mixture was raised from 25 to 65° C.
  2. customAt temperature 50-52° C
  3. temperatureThe reaction mixture was cooled from 52° C. to 5° C.
  4. stirringstirred for 5 min
  5. stirringLater the reaction mixture was stirred at 25-30° C. for 12 hrs
  6. customthe thick precipitate obtained
  7. filtrationwas filtered
  8. washwashed with 5 mL of acetone
  9. customthe residue was dried in a vacuum oven

Sources & evidence

ORD record
ord-560a7c313eb24d96883617b184fc093d
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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