Hydrochloric Acid → diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-hydroxypropylphosphonate

HRID 1706186Notes

Reaction equation

HRID 1706186 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:13][CH:14]([O:24]C1CCCCO1)[CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[O:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:5])[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4]([N:6]([CH2:13][CH:14]([OH:24])[CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[O:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20337196diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-(tetrahydro-2H-pyran-2-yloxy)propylphosphonate

Product 1

HCID 20337198diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-hydroxypropylphosphonateYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-(tetrahydro-2H-pyran-2-yloxy)propylphosphonate (54.0 g.), ethanol (100 ml.) and 0.1 N hydrochloric acid (100 ml.) was stirred for 4 hours at ambient temperature. After the reaction was completed, the ethanol was distilled off from the reaction mixture under reduced pressure to give an aqueous solution, which was extracted three times with ethyl acetate (200 ml. once and 50 ml. twice). The combined extracts were washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated to dryness under reduced pressure to give oily diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-2-hydroxypropylphosphonate (39.25 g.).

Workup

  1. distillationthe ethanol was distilled off from the reaction mixture under reduced pressure
  2. customto give an aqueous solution, which
  3. extractionwas extracted three times with ethyl acetate (200 ml
  4. washThe combined extracts were washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d0359736582f4862aa085d9391d4ab13
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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