Tin tetrachloride dihydrate → [(15)-2-(3,5-Dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl] 3-aminobenzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:33])[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>O1CCCC1>[NH2:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([O:20][C@H:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[CH2:8][C:7]1[C:2]([Cl:1])=[CH:3][N+:4]([O-:33])=[CH:5][C:6]=1[Cl:32])=[O:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a stirred solution of [(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-3-nitrobenzoate (0.640 g, 1.30 mmol) in anhydrous tetrahydrofuran (30.0 mL) was added tin chloride dihydrate (1.18 g, 5.2 mmol). After heating at 75° C. for 16 hours, the reaction was allowed to cool to room temperature. The reaction was partitioned between ethyl acetate and sodium bicarbonate and extracted with ethyl acetate (×2). The combined organic extracts were dried on magnesium sulphate, filtered and the solvent was removed in vacuo to afford the title compound as a brown solid (0.520 g, 87% yield).
Workup
- temperatureto cool to room temperature
- customThe reaction was partitioned between ethyl acetate and sodium bicarbonate
- extractionextracted with ethyl acetate (×2)
- customThe combined organic extracts were dried on magnesium sulphate
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-7ad455ae9c87442ca99cd0da8b69f519
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090606B2
Reaction notes
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