Ammonia → HCID 20337233, compound

HRID 1706231Notes

Reaction equation

HRID 1706231 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[OH:8][NH:9][CH2:10][CH2:11][CH2:12][P:13](=[O:16])([OH:15])[OH:14].FC(F)(F)C(OC(=O)C(F)(F)F)=O.N>C(O)C.O>[OH:8][N:9]([CH2:10][CH2:11][CH2:12][P:13](=[O:14])([OH:16])[OH:15])[C:3](=[O:4])[C:2]([F:7])([F:6])[F:1]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydride2×HCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 20337233HCID 20337233, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (4 ml) was added to 3-(N-hydroxyamino)propylphosphonic acid (1.55 g). After the mixture was stirred at ambient temperature for 15 minutes, to the mixture was added trifluoroacetic anhydride (2.52 g) with stirring under ice-cooling. After the stirring was continued at the same temperature for 1.5 hours, to the mixture was further added trifluoroacetic anhydride (2.73 g). The mixture was further stirred for an hour. Then, the resultant mixture was concentrated under reduced pressure to give a residue, which was dissolved in ethanol (10 ml). The solution was adjusted to pH 6-7 with aqueous ammonia, stirred for an hour under ice-cooling and concentrated under reduced pressure to give a residue, which was subjected to a column chromatography on cellulose (100 ml). This column was washed with isopropylalcohol (200 ml) and then the object compound was eluted with a mixture of isopropyl alcohol and water (9:1 ) (200 ml). The eluate was concentrated under reduced pressure to give a residue, which was pulverized with a mixture of ethanol and water to give powdery monoammonium salt of 3-(N-hydroxy-N-trifluoroacetylamino)propylphosphonic acid (0.2 g).

Workup

  1. stirringwith stirring under ice-
  2. temperaturecooling
  3. waitAfter the stirring was continued at the same temperature for 1.5 hours, to the mixture
  4. stirringThe mixture was further stirred for an hour
  5. concentrationThen, the resultant mixture was concentrated under reduced pressure
  6. customto give a residue, which
  7. stirringstirred for an hour under ice-
  8. temperaturecooling
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue, which
  11. washThis column was washed with isopropylalcohol (200 ml)
  12. washthe object compound was eluted with a mixture of isopropyl alcohol and water (9:1 ) (200 ml)
  13. concentrationThe eluate was concentrated under reduced pressure
  14. customto give a residue, which

Sources & evidence

ORD record
ord-fe315a03af054273b9ba0f8bfcef0e24
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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