Trifluoroacetic acid → HCID 131718862, compound

HRID 864491Notes

Reaction equation

HRID 864491 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[C:14]([OH:16])=O)=[O:8])=[CH:3][CH:2]=1.[F:26][C:27]([F:32])([F:31])C(O)=O>>[OH2:8].[F:26][C:27]([F:32])([F:31])[C:14]([CH:13]([NH:17][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:16]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 184849N~2~,N~5~-Bis[hydroxy(phenyl)methylidene]ornithine

Product 1

HCID 131718862HCID 131718862, compound

Procedure

A mixture of the ornithuric acid, as described in Step A, (501.5 g, 1.47 mol) and trifluoroacetic acid (TFAA) (400 ml) was stirred at room temperature for one hour. The resulting solution was evaporated (0.1 Torr) and 1 L of TFAA was added. The solution was stirred for 16 hours and evaporated to dryness (0.01 Torr). Further 1 L of TFAA was added and the solution stirred for 4 hours. Reevaporation of the solution to dryness (0.1 Torr) was followed by addition of further 500 ml of TFAA. The solution was stirred for another 16 hours and evaporated to dryness (0.1 Torr). The oily residue was dissolved in 1.6 L of anhydrous THF and freshly dehydrated oxalic acid (440 g) added to the solution over a period of two hours. Stirring of the mixture was continued for 16 hours, when 7.5 L of ethyl acetate was added. The solution was washed with brine, aqueous sodium bicarbonate (4X), and brine, dried over MgSO4 and evaporated to dryness. Yield of the title compound: 522.8 g (90.5%). Rf=0.33 and 0.27 (eluent: ethyl acetate/petroleum ether 1:1), ketone and its hydrate. m.p.: 113°-115° C.

Workup

  1. customThe resulting solution was evaporated (0.1 Torr) and 1 L of TFAA
  2. additionwas added
  3. stirringThe solution was stirred for 16 hours
  4. customevaporated to dryness (0.01 Torr)
  5. additionFurther 1 L of TFAA was added
  6. stirringthe solution stirred for 4 hours
  7. customReevaporation of the solution to dryness (0.1 Torr)
  8. additionwas followed by addition of further 500 ml of TFAA
  9. stirringThe solution was stirred for another 16 hours
  10. customevaporated to dryness (0.1 Torr)
  11. dissolutionThe oily residue was dissolved in 1.6 L of anhydrous THF
  12. additionfreshly dehydrated oxalic acid (440 g) added to the solution over a period of two hours
  13. stirringStirring of the mixture
  14. waitwas continued for 16 hours
  15. additionwhen 7.5 L of ethyl acetate was added
  16. washThe solution was washed with brine, aqueous sodium bicarbonate (4X), and brine
  17. dry with materialdried over MgSO4
  18. customevaporated to dryness

Sources & evidence

ORD record
ord-b8604c6a6c5c4ff9b85c012bbedb3c5b
Source dataset
uspto-grants-1996_10
Patent number
US05563156

Reaction notes

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