Ethyl 3-amino-2-(4-methoxyphenyl)propyl(diethoxymethyl)phosphinate → 3-Amino-2-(4-methoxyphenyl)propylphosphonous acid
Reaction equation
[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC>Cl>[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:4][P:5]([OH:6])[OH:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4.6 g of ethyl 3-amino-2-(4-methoxyphenyl)propyl(diethoxymethyl)phosphinate in 30 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 1 hour. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure and co-evaporated twice with 20 ml of water under reduced pressure. The crude product is dissolved in 20 m l of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-2-(4-methoxyphenyl)propylphosphonous acid (1/2 M H2O), m.p. 260°-265° C., 31 p=+24.5 ppm (D2O).
Workup
- temperatureto reflux for a period of 1 hour
- concentrationconcentrated under reduced pressure
- dissolutionThe crude product is dissolved in 20 m l of water
- washwashed twice with 20 ml of diethyl ether
- customthe aqueous layer is then separated
- customevaporated under reduced pressure
- dissolutionThe crude product is dissolved in 50 ml ethanol
- addition5 ml of propylene oxide is added dropwise
- filtrationThe precipitated solid is collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-69da6c03210744a88b96b49ba2d9248a
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05457095
Reaction notes
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