Benzyl Alcohol → dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate
Reaction equation
[NH2:1][CH:2](/[CH:9]=[C:10](/[CH2:19][P:20]([OH:23])([OH:22])=[O:21])\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]C=1.Cl>C(Cl)Cl>[NH2:1][CH:2](/[CH:9]=[C:10](/[CH2:19][P:20]([OH:23])([OH:22])=[O:21])\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:10]=[CH:9][CH:2]=[CH:3][CH:4]=1)=[O:5]Participants
5
Procedure
To 3.25 g (10 mmol) of diethyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate and 10.8 g (100 mmol) of benzyl alcohol are added 10 ml of methylene chloride and 20 ml of 4N ethereal hydrochloric acid, and the mixture is allowed to stand for 1 week. The mixture is then evaporated to dryness, and the residue is dissolved in 25 ml of ethanol. To this solution is then added dropwise a solution of 15 ml of propylene oxide in 15 ml of ethanol. The readily volatile constituents are removed by evaporation under reduced pressure, affording dibenzyl E-2-amino-4-phosphonomethyl-hept-3-ene-1,7-dicarboxylate.
Workup
- waitto stand for 1 week
- customThe mixture is then evaporated to dryness
- dissolutionthe residue is dissolved in 25 ml of ethanol
- additionTo this solution is then added dropwise a solution of 15 ml of propylene oxide in 15 ml of ethanol
- customThe readily volatile constituents are removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-11b9f31957fd49278d2f7b588abfdae7
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134134
Reaction notes
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