Ethyl bromoacetate → Ethyl 2-(benzyl((diethoxyphosphoryl)methyl)amino)acetate
Reaction equation
[CH2:1]([NH:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(#N)C>[CH2:1]([N:8]([CH2:9][P:10]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:17])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Procedure
Into a 500-mL 3-necked round-bottom flask, was placed a solution of diethyl (benzylamino)methylphosphonate (intermediate 5.2) (12 g, 46.69 mmol, 1.00 equiv) in acetonitrile (150 mL), DIEA (12 g, 2.00 equiv). This was followed by the addition of ethyl 2-bromoacetate (8.4 g, 50.30 mmol, 1.10 equiv) dropwise with stirring. The mixture was stirred for 30 min at room temperature. The resulting solution was heated to reflux for 6 hr. The resulting mixture was cooled to room temperature and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20 to 1:5). This resulted in 8.0 g (50%) of ethyl 2-(benzyl((diethoxyphosphoryl)methyl)amino)acetate as yellow oil.
Workup
- customInto a 500-mL 3-necked round-bottom flask, was placed
- stirringThe mixture was stirred for 30 min at room temperature
- temperatureThe resulting solution was heated
- temperatureto reflux for 6 hr
- concentrationconcentrated under vacuum
- customThis resulted in 8.0 g (50%) of ethyl 2-(benzyl((diethoxyphosphoryl)methyl)amino)acetate as yellow oil
Sources & evidence
- ORD record
- ord-b93065fe4edc44bc8ef747f5762aaa6a
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969377B2
Reaction notes
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