Water → Trifluoroacetic acid

HRID 728622Notes

Reaction equation

HRID 728622 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].O.C(OC([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([N:26]1[CH:33]=[C:32]([F:34])[C:30](=[O:31])[NH:29][C:27]1=[O:28])=[O:25])=O)(C)(C)C.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([N:26]1[CH:33]=[C:32]([F:34])[C:30](=[O:31])[NH:29][C:27]1=[O:28])=[O:25].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 6422Trifluoroacetic acidHCID 149978561-[6-(t-Butoxycarbonylamino)-n-hexylcarbamoyl]-5-fluorouracil

Product 2

HCID 6422Trifluoroacetic acidHCID 149978571-(6-Amino-n-hexylcarbamoyl)-5-fluorouracil

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of a mixed solution of anhydrous trifluoroacetic acid: water=9:1 was suspended 0.74 g (2 mmole) of 1-[6-(t-butoxycarbonylamino)-n-hexylcarbamoyl]-5-fluorouracil under ice-cooling. When the suspension was stirred under ice-cooling, it was gradually dissolved to form a uniform solution. After stirring about one hour, the mixture was condensed under reduced pressure. To the residue was added 50 ml of toluene, and azeotropically dehydrated by reduced pressure condensation. To the residue was again added 50 ml of toluene, the same procedure as mentioned above was carried out. When about 100 ml of chloroform was added to the residue and allowed to stand overnight, the residue crystallized. Chloroform was removed under reduced pressure and the residue was recrystallized from 20 ml of ethanol. The title compound can be obtained with an amount of 0.29 g (Yield: 37.5%) as a salt of trifluoroacetic acid with a molar ratio of 1:1.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. dissolutionit was gradually dissolved
  4. customto form a uniform solution
  5. stirringAfter stirring about one hour
  6. customcondensed under reduced pressure
  7. customazeotropically dehydrated by reduced pressure condensation
  8. customthe residue crystallized
  9. customChloroform was removed under reduced pressure
  10. customthe residue was recrystallized from 20 ml of ethanol

Sources & evidence

ORD record
ord-e0a7838d59b5458e81dbca65c1826b25
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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