Tetrahydrofuran → HCID 67256387, compound
Reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=[O:34])[C:23](=[C:35](SC)SC)[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-:41].[Na+].[O:43]1[CH2:47]CCC1>CO.Cl>[C:1]([O:5][C:6]([NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:24](=[O:34])[CH:23]([C:35]([O:43][CH3:47])=[O:41])[CH2:22][CH2:21][C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)=[O:40])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of tert-butyl(1-(4-(6-(bis(methylthio)methylene)-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)phenyl)cyclobutyl)carbamate (140 mg, 0.24 mmol) in anhydrous tetrahydrofuran (2.8 mL) was added a solution of sodium hydroxide (96 mg, 2.4 mmol) in methanol (2.2 mL). The reaction mixture was heated to 50° C. under a nitrogen atmosphere for 2 hours. After allowing to cool to room temperature the mixture was diluted with 1M HCl solution (3 mL) and extracted into ethyl acetate (3×6 mL). The combined organic phases were washed with brine (3×6 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the desired product as a brown solid (126 mg, quantitative yield). LCMS (Method A) RT=7.56 min, M+H+=527.14.
Workup
- temperatureto cool to room temperature the mixture
- extractionextracted into ethyl acetate (3×6 mL)
- washThe combined organic phases were washed with brine (3×6 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-ab25e5d0a375469cab9402cc9c06797d
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221838B2
Reaction notes
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