Sulfuric Acid → Clopidogrel hydrogen sulfate

HRID 988856Notes

Reaction equation

HRID 988856 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
27.5 °C

Procedure

To 1.98 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 50-52° C. and within one lot 0.7 g of concentrated H2SO4 (95%) was added with constant stirring and the reaction mixture was suddenly cooled to 0° C. to −5° C. for 10 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 (1.6 g, 62%) was dried in a vacuum oven.

Workup

  1. additionwas added
  2. stirringwith constant stirring
  3. temperaturethe reaction mixture was suddenly cooled to 0° C. to −5° C. for 10 min
  4. stirringLater the reaction mixture was stirred at 25-30° C. for 12 hrs
  5. customthe thick precipitate obtained
  6. filtrationwas filtered
  7. washwashed with 5 mL of acetone
  8. dry with materialthe residue (1.6 g, 62%) was dried in a vacuum oven

Sources & evidence

ORD record
ord-0ce00ecc162744efadbc8e7c383745fd
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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