Dimethylformamide → N-Methyl-N-methoxy-4-methyl-3-phenylpentaneamide
Reaction equation
[CH3:1][N:2](C)[CH:3]=[O:4].C(P(=O)(OCC)[O:9][CH2:10]C)#N.[CH3:16][CH:17]([CH3:29])[CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19]C(O)=O>C(N(CC)CC)C.O1CCCC1>[CH3:1][N:2]([O:9][CH3:10])[C:3](=[O:4])[CH2:19][CH:18]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:17]([CH3:16])[CH3:29]Participants
6
Procedure
Under a nitrogen atmosphere, a dimethylformamide solution of diethyl cyanophosphonate (1.97 g) and triethylamine (1.63 mL) was added to a tetrahydrofuran solution (24 mL) of 4-methyl-3-phenyl-pentanoic acid (1.96 g), N, O—dimethylhydroxyamine hydrochloride (1.18 g) and triethylamine (1.63 mL) at 0° C. After 19 hours, the organic layer was separated by adding diethyl ether and an aqueous saturated ammonium chloride thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the mixture was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system), to give the title compound (1.13 g, 47%).
Workup
- customthe organic layer was separated
- additionby adding diethyl ether
- washThe resulting organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtering off the drying agent
- customthe mixture was evaporated
- customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system)
Sources & evidence
- ORD record
- ord-9d321dfe17ac4339af3d30f67b490ab6
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06906072B1
Reaction notes
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