Potassium → diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)propylphosphonate

HRID 2051970Notes

Reaction equation

HRID 2051970 reaction equation
Cl[CH2:2][CH2:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[K].[CH2:14]([O:16][C:17]([O:19][NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])=[O:18])[CH3:15]>CN(C)C=O>[CH2:23]([O:22][C:21]([N:20]([CH2:2][CH2:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[O:19][C:17]([O:16][CH2:14][CH3:15])=[O:18])=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 5462222PotassiumHCID 11446651Ethyl EthoxycarbonyloxycarbamateHCID 133232971-Chloro-3-diethoxyphosphoryl-propane

Product 1

HCID 20337213diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)propylphosphonateYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl 3-chloropropylphosphonate (430.6 g) in dry N,N-dimethyformamide (2.25 l) was added potassium salt of ethyl N-ethoxycarbonyloxycarbamate (429.2 g). This mixture was stirred at 64°-66° C. for three hours. After the resulting potassium chloride was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (2.0 l) and washed with water (4.0 l). The aqueous layer was extracted twice with ethyl acetate (1.2 and 0.8 l). The combined ethyl acetate layer was washed with saturated aqueous sodium chloride solution (1.5 l), dried over magnesium sulfate and concentrated under reduced pressure to give oily diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)propylphosphonate (643.7 g).

Workup

  1. customAfter the resulting potassium chloride was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (2.0 l)
  4. washwashed with water (4.0 l)
  5. extractionThe aqueous layer was extracted twice with ethyl acetate (1.2 and 0.8 l)
  6. washThe combined ethyl acetate layer was washed with saturated aqueous sodium chloride solution (1.5 l)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eceaead44d384a72bfa3c08dc4acdc4b
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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