Nitric Acid → HCID 54421190, compound

HRID 274955Notes

Reaction equation

HRID 274955 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C@H:6]([C:18]([OH:20])=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)=[O:4].[N:23]([O-:25])=[O:24].[Na+].[N+]([O-])(O)=O.C(OCC)(=O)C>C(O)(=O)C.C(OC(=O)C)(=O)C>[F:1][C:2]([F:21])([F:22])[C:3]([NH:5][C@H:6]([C:18]([OH:20])=[O:19])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[C:12]([N+:23]([O-:25])=[O:24])[CH:13]=1)=[O:4]

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 54027150HCID 54027150, compound

Product 1

HCID 54421190HCID 54421190, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
10 °C

Procedure

63.2 g (0.2 Mol) of N-trifluoroacetyl-4-acetylaminophenylalanine are suspended in 300 ml of glacial acetic acid and 100 ml of acetic anhydride. After the solution has been cooled to 10° C., 1.5 g (0.022 Mol) of sodium nitrite are added and then 33.14 ml (0.8 Mol) of fuming nitric acid are slowly added dropwise, during which time a solution is formed. After stirring for 2 hours at 0° C. the mixture is poured onto 1 kg of ice and extracted 3 times with 250 ml of ethyl acetate. After the organic phase has been dried the mixture is concentrated by evaporation, the resulting residue is mixed twice with a mixture of 150 ml of ethyl acetate and 150 ml of toluene and evaporated down again. The residue obtained this time is combined with 100 ml of ethyl acetate cooled to -10° C., suction filtered and washed again with ethyl acetate cooled to -10° C.

Workup

  1. customis formed
  2. extractionextracted 3 times with 250 ml of ethyl acetate
  3. customAfter the organic phase has been dried the mixture
  4. concentrationis concentrated by evaporation
  5. additionthe resulting residue is mixed twice with a mixture of 150 ml of ethyl acetate and 150 ml of toluene
  6. customevaporated down again
  7. customThe residue obtained this time
  8. temperaturecooled to -10° C.
  9. filtrationsuction filtered
  10. washwashed again with ethyl acetate
  11. temperaturecooled to -10° C.

Sources & evidence

ORD record
ord-a5bacf6ce7c7481eb0eebd575aba3f30
Source dataset
uspto-grants-1995_02
Patent number
US05391556

Reaction notes

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