Stannous Chloride → (S)-3-Amino-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)benzonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]([CH3:14])([CH3:13])[O:11][C:10](=[O:15])[N:9]2[CH:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=3[N+:31]([O-])=O)[CH2:18][CH2:17]2)=[CH:4][CH:3]=1.[Sn](Cl)Cl>CCO>[NH2:31][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:23]=1[NH:22][CH:19]1[CH2:20][CH2:21][CH:16]([N:9]2[C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]([CH3:13])([CH3:14])[O:11][C:10]2=[O:15])[CH2:17][CH2:18]1)[C:27]#[N:28]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a flask charged with (S)-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)-3-nitrobenzonitrile (0.490 g, 1.083 mmol) was added EtOH (4.33 mL) followed by tin (II) chloride (0.616 g, 3.25 mmol). The resulting yellow suspension was heated overnight at 80° C. LC-MS analysis of the resulting suspension indicated about 90% conversion to the desired product (215 nm). Additional EtOH (4 mL) was added to aid solubilization and additional SnCl2 was added (300 mg). The resulting mixture was heated at 80° C. After 1 hour, LC-MS indicated complete conversion. The yellow suspension was dried under reduced pressure and the residue was purified with a 50 g SNAP column ramping DCM:MeOH (90:10) in DCM (0-30%, then isocratic at 30%, detection at 215 nm) to provide (S)-3-amino-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)benzonitrile (0.156 g, 0.369 mmol, 34.1% yield) as a brown oil and as a mixture of isomers with impurities present (˜20% based on LC-MS). The material was used in the next step without further purification. m/z (ESI) 423.2 (M+H)+.
Sources & evidence
- ORD record
- ord-a18dc0e2ca7e4fb4b9b567c399fc74a1
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340549B2
Reaction notes
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