Sodium Hydroxide → [3-Amino-2-(4-chloro-phenyl)-propyl]-diethoxymethyl-phosphinic acid

HRID 973589Notes

Reaction equation

HRID 973589 reaction equation
[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6]CC.[OH-].[Na+]>CO>[NH2:1][CH2:2][CH:3]([C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:6])[OH:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14362833Ethyl 3-amino-2-(p-chlorophenyl)propyl(diethoxymethyl)phosphinate

Product 1

HCID 9923821[3-Amino-2-(4-chloro-phenyl)-propyl]-diethoxymethyl-phosphinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g of ethyl 3-amino-2-(p-chlorophenyl)-propyl(diethoxymethyl)phosphinate in 5 ml of methanol are added 2.5 ml of a 2 normal sodium hydroxide solution and the mixture is heated to a temperature of 80° for a period of 5 hours. After this time, the reaction is concentrated under reduced pressure, and the oily residue is passed down an Ion Exchange Resin (DOWEX® 50W-X8 H+) using de-ionised water as eluant. Ninhydrin-positive fractions are combined and evaporated to give 3-amino-2-(4-chlorophenyl)-propyl(diethoxymethyl)phosphinic acid, m.p. 175°-185° (dec.), 31P-NMR : δ=+31.6 ppm (D2O).

Workup

  1. temperaturethe mixture is heated to a temperature of 80° for a period of 5 hours
  2. concentrationAfter this time, the reaction is concentrated under reduced pressure
  3. customevaporated

Sources & evidence

ORD record
ord-89eaa8f668244491ad3d36043bd9f03f
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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