Sulfuric Acid → Clopidogrel bisulfate
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].[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>C(O)CCCCC>[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].[OH:25][S:22]([OH:26])(=[O:24])=[O:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 27.5 °C
Procedure
Clopidogrel base (250 gms) was dissolved in n-hexanol (1.25 L) with stirring at 25 to 30° C. Dilute sulfuric acid was added at 10 to 15° C. The reaction mixture was seeded with form-I crystals at 20 to 25° C. The reaction mixture was stirred at room temperature, for 10-12 hrs and subsequently it was stirred at 22 to 25° C., for 1-3 hours at high agitation. The reaction mixture was further stirred for 5-8 hours at a room temperature at low agitation. It was then filtered, washed with methyl tert butyl ether (750 ml) and dried at 30 to 35° C. in a drier, to obtain 240 g of clopidogrel bisulfate salt. Subsequent analysis confirmed that the crystals were clopidogrel hydrogen sulfate Form-I.
Workup
- customwas seeded with form-I crystals at 20 to 25° C
- stirringThe reaction mixture was stirred at room temperature, for 10-12 hrs
- stirringsubsequently it was stirred at 22 to 25° C., for 1-3 hours at high agitation
- stirringThe reaction mixture was further stirred for 5-8 hours at a room temperature at low agitation
- filtrationIt was then filtered
- washwashed with methyl tert butyl ether (750 ml)
- customdried at 30 to 35° C. in a drier
Sources & evidence
- ORD record
- ord-6441e6fdccd944e6a6196f22b316fcd5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08907090B2
Reaction notes
Loading…