4-Chloroaniline → methyl(2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoate
Reaction equation
[CH:1]1([C@H:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1>C(#N)C>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:9](=[O:11])[CH2:8][C@H:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:12]([O:14][CH3:15])=[O:13])=[CH:19][CH:18]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of (3R)-3-cyclohexyl-4-methoxy-4-oxobutanoic acid (0.21 g), 4-chloroaniline (0.13 g) and HOBt (0.23 g) in acetonitrile (10 ml) were added WSC (0.29 g) and N-methylmorpholine (0.10 g), and mixed at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed sequentially with an aqueous sodium hydrogen carbonate solution, water, a 5% aqueous citric acid solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a pale brown solid (0.30 g, 93%).
Workup
- additionmixed at room temperature for 15 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate
- washThe ethyl acetate solution was washed sequentially with an aqueous sodium hydrogen carbonate solution, water
- dry with materiala 5% aqueous citric acid solution and saturated brine, and dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-6096523440a24c799c599e6733b97686
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820673B2
Reaction notes
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