Dimethylformamide → diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-methylpropylphosphonate

HRID 2051973Notes

Reaction equation

HRID 2051973 reaction equation
Cl[CH2:2][CH:3]([CH3:13])[CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[K].[CH2:15]([O:17][C:18]([O:20][NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])=[O:19])[CH3:16].CN(C)C=O>C(OCC)(=O)C.O>[CH2:24]([O:23][C:22]([N:21]([CH2:2][CH:3]([CH3:13])[CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[O:20][C:18]([O:17][CH2:15][CH3:16])=[O:19])=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 5462222PotassiumHCID 11446651Ethyl EthoxycarbonyloxycarbamateHCID 20337215Diethyl 3-chloro-2-methylpropylphosphonate

Product 1

HCID 20337240diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-methylpropylphosphonateYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of diethyl 3-chloro-2-methylpropylphosphonate (22.8 g.), potassium salt of ethyl N-ethoxycarbonyloxycarbamate (21.5 g.) and dry N,N-dimethylformamide (114 ml.) was stirred at 80°-85° C. for 3 hours and then concentrated under reduced pressure to give an oily residue, to which was added a mixture of water (100 ml.) and ethyl acetate (100 ml.) The ethyl acetate layer was separated and the resultant aqueous layer was saturated with sodium chloride and extracted again with ethyl acetate (50 ml.). The combined ethyl acetate layer was washed with aqueous solution saturated with sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give oily diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-methylpropylphosphonate (30.2 g.).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give an oily residue
  3. additionto which was added
  4. customwas separated
  5. extractionextracted again with ethyl acetate (50 ml.)
  6. washThe combined ethyl acetate layer was washed with aqueous solution saturated with sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a50c96582fd049d3b5b4ffb88558c614
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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