Ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate → 3-Amino-2-benzylpropylphosphonous acid

HRID 2209943Notes

Reaction equation

HRID 2209943 reaction equation
[NH2:1][CH2:2][CH:3]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC>Cl>[NH2:1][CH2:2][CH:3]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][P:5]([OH:9])[OH:6]

Participants

3

Reactant 1

HCID 14362816Ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate

Product 1

HCID 104657993-Amino-2-benzylpropylphosphonous acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3.5 g of ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate in 35 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 3 hours. 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 ml 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-benzylpropylphosphonous acid, m.p. 205°-212° C., 31 p=+26.1 ppm (D2O).

Workup

  1. temperatureto reflux for a period of 3 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude product is dissolved in 20 ml of water
  4. washwashed twice with 20 ml of diethyl ether
  5. customthe aqueous layer is then separated
  6. customevaporated under reduced pressure
  7. dissolutionThe crude product is dissolved in 50 ml ethanol
  8. addition5 ml of propylene oxide is added dropwise
  9. filtrationThe precipitated solid is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-49cf2f8973914328ac1abe83af24ddda
Source dataset
uspto-grants-1995_10
Patent number
US05457095

Reaction notes

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