Dimethylformamide → methyl (3R)-3-methyl-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C@@H:5]([CH3:9])[C:6](O)=[O:7].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:22][N:23]1[CH:27]=[CH:26][C:25]([NH2:28])=[N:24]1>C1COCC1.C(N(CC)CC)C>[CH3:9][C@@H:5]([C:6]([NH:28][C:25]1[CH:26]=[CH:27][N:23]([CH3:22])[N:24]=1)=[O:7])[CH2:4][C:3]([O:2][CH3:1])=[O:10]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2R)-4-methoxy-2-methyl-4-oxobutanoic acid (0.30 mL) and DMF (20 μL) in THF (5.0 mL) was added oxalyl chloride (0.25 mL). The reaction mixture was stirred at room temperature for 3 hr, and 1-methyl-1H-pyrazol-3-amine (200 mg) and triethylamine (0.62 mL) were added thereto. The reaction mixture was stirred at room temperature for 15 hr, and extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (345 mg).
Workup
- stirringThe reaction mixture was stirred at room temperature for 15 hr
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-feabc95f857c4127bdd96206ec5c5a90
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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