Clopidogrel → Clopidogrel 2-naphthalenesulfonate
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].O.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[S:33]([OH:36])(=[O:35])=[O:34]>C(OCC)(=O)C.O>[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].[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[S:33]([O-:36])(=[O:35])=[O:34]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
50 g of clopidogrel free base having an optical purity of 99.3% ee which was prepared by the method similar to that disclosed in International Patent Publication No. WO 02/59128 was dissolved in 100 ml of ethyl acetate, and a solution containing 34.8 g of 2-naphthalenesulfonic acid monohydrate dissolved in a mixture of 150 ml of ethyl acetate and 5 ml of water was added thereto dropwise over a period of 30 minutes. Then, the mixture was stirred at room temperature for 12 hours, and then, at a temperature ranging from 0 to 5 for 4 hours. The precipitates formed were filtered, washed with 30 ml of ethyl acetate and dried at 50° C., to obtain 71.6 g of the title compound (yield: 87%) as an white crystal.
Workup
- customwas prepared by the method similar to
- additionwas added
- waitat a temperature ranging from 0 to 5 for 4 hours
- customThe precipitates formed
- filtrationwere filtered
- washwashed with 30 ml of ethyl acetate
- customdried at 50° C.
Sources & evidence
- ORD record
- ord-04e1bd4d6be64363b8ddd9572cef2070
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470707B2
Reaction notes
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