Sulfuric Acid → Clopidogrel hydrogen sulfate

HRID 988854Notes

Reaction equation

HRID 988854 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 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

2.1 g (+)-Methyl (2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetate was added 7.6 mL of acetone to obtain a clear solution. To this solution, 0.887 g of H2SO4 (80%) was added slowly and temperature was maintained around 20° C. under nitrogen atmosphere. Later the reaction mixture was cooled upto −20° C. for 2 hrs and then the temperature was brought to room temperature (20° C.). The reaction mixture was stirred at 20-25° C. Precipitate was isolated (600 mg), dried under vacuum at temperature not exceeding 50° C.

Workup

  1. customto obtain a clear solution
  2. temperatureLater the reaction mixture was cooled upto −20° C. for 2 hrs
  3. customwas brought to room temperature
  4. custom(20° C.)
  5. customPrecipitate was isolated (600 mg)
  6. customdried under vacuum at temperature not
  7. customexceeding 50° C.

Sources & evidence

ORD record
ord-67dbd3d4c9804ae69acf199e525efbef
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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