Sulfuric acid magnesium salt (1:1) → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(4-formylthiazol-2-ylthio)acetamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:7]1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH:22]=[O:23])[N:21]=2)[CH2:7]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The resultant product (1.53 g) of (70-1) was dissolved in chloroform (10 mL), magnesium sulfate (500 mg) was added, manganese dioxide (1.35 g) was further added, and the mixture was stirred overnight at room temperature. Magnesium sulfate (500 mg) and manganese dioxide (1.35 g) were further added and the mixture was stirred at room temperature for 7 hrs. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (643 mg) as a colorless oil.
Workup
- stirringthe mixture was stirred at room temperature for 7 hrs
- filtrationThe reaction mixture was filtered through celite
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
- customThe solvent was evaporated from the eluent
Sources & evidence
- ORD record
- ord-0be846eb0e0e405da4a9664bff148cc4
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935700B2
Reaction notes
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