Diethyl Ether → 3-(N-aminoacetyl-N-hydroxyamino)propylphosphonic acid

HRID 2051994Notes

Reaction equation

HRID 2051994 reaction equation
Br.C(O)(=O)C.C(OC([NH:16][CH2:17][C:18]([N:20]([CH2:22][CH2:23][CH2:24][P:25](=[O:28])([OH:27])[OH:26])[OH:21])=[O:19])=O)C1C=CC=CC=1.C(OCC)C>C(O)(=O)C>[NH2:16][CH2:17][C:18]([N:20]([CH2:22][CH2:23][CH2:24][P:25](=[O:26])([OH:28])[OH:27])[OH:21])=[O:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 539241393-[N-(N-benzyloxycarbonylaminoacetyl)N-hydroxyamino]propylphosphonic acid

Product 1

HCID 540487663-(N-aminoacetyl-N-hydroxyamino)propylphosphonic acidYield 32.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

48% Hydrogen bromide-acetic acid (1 ml) was added under ice-cooling to a solution of 3-[N-(N-benzyloxycarbonyl-aminoacetyl)-N-hydroxyamino]propylphosphonic acid (200 mg) in acetic acid (1 ml) and the reaction mixture was stirred at an ambient temperature for an hour. To the resultant mixture was added dry ethyl ether (20 ml) to precipitate an oil. The oil was separated, washed twice with dry ethyl ether (10 ml) and then dissolved in water (0.5 ml). The solution was adjusted to pH 4 with pyridine and ethanol (5 ml) was added thereto to give precipitates. The upper layer was removed by decantation and the precipitates was pulverized with ethyl ether (10 ml) to give 3-(N-aminoacetyl-N-hydroxyamino)propylphosphonic acid (40 mg) in the form of powder.

Workup

  1. customto precipitate an oil
  2. customThe oil was separated
  3. washwashed twice with dry ethyl ether (10 ml)
  4. dissolutiondissolved in water (0.5 ml)
  5. additionwas added
  6. customto give
  7. customprecipitates
  8. customThe upper layer was removed by decantation

Sources & evidence

ORD record
ord-f68c63221e89444f8af1fb45d3b4ede1
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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