Acetonitrile → Clopidogrel metabolite h4
Reaction equation
[ClH:1].[S:2]1[CH:10]2[C:5]([CH2:6][NH:7][CH2:8][CH2:9]2)=[CH:4]C1=O.[C:12](=[O:15])([O-:14])[O-].[Na+].[Na+].[C:18](=[O:21])(O)[O-:19].[Na+].[C:23](#N)[CH3:24]>>[CH:9]1[CH:10]=[CH:5][C:4]([Cl:1])=[C:23]([C@H:24]([N:7]2[CH2:6]/[C:5](=[CH:4]\[C:18]([OH:19])=[O:21])/[CH:10]([SH:2])[CH2:9][CH2:8]2)[C:12]([OH:14])=[O:15])[CH:8]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
In a four necked round bottomed flask, under nitrogen atmosphere, 1000 ml acetonitrile, 49.5 gm of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one HCl, 55 gm of sodium carbonate and 100 gm of Methyl (7)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate were added and the mixture was heated to about 50° C. After reaction, reaction mass was filtered, filtrate concentrated and concentrated mass was taken in dichloromethane, washed with water and concentrated under reduced pressure. The oily residue was treated with IPA.HCl solution in isopropanol (IPA) and filtered to obtain the mixture of isomers as hydrochloride salt. To it sodium bicarbonate solution was added till pH turned alkaline. The product was then extracted in dichloromethane (MDC). The MDC layer was washed with water, dried and distilled to obtain the product as an oily residue.
Workup
- customAfter reaction, reaction mass
- filtrationwas filtered
- concentrationfiltrate concentrated
- concentrationconcentrated mass
- washwashed with water
- concentrationconcentrated under reduced pressure
- additionThe oily residue was treated with IPA
- filtrationHCl solution in isopropanol (IPA) and filtered
- customto obtain
- extractionThe product was then extracted in dichloromethane (MDC)
- washThe MDC layer was washed with water
- customdried
- distillationdistilled
- customto obtain the product as an oily residue
Sources & evidence
- ORD record
- ord-56b066127d5f4597aa864e788059676c
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536337B2
Reaction notes
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