Trifluoroacetic acid → HCID 10402602, compound

HRID 1198152Notes

Reaction equation

HRID 1198152 reaction equation
FC(F)(F)C(O)=O.[C:8]1(/[C:14](=[N:21]\[O:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])/[CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>>[C:8]1(/[C:14](=[N:21]\[O:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])/[CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 10089718HCID 10089718, compound

Product 1

HCID 10402602HCID 10402602, compoundYield 57%

Conditions

Temperature
-10 °C

Procedure

Trifluoroacetic acid (1.3 ml) is added dropwise at -10° C. to 0.23 g (0.643 mmoles) of tert-butyl (E)-5-[1-phenyl-2-(imidazol-1-yl)ethylidene]aminoxypentanoate. The mixture is stirred at -10° C. for 1 hour and 30 minutes. A cooled saturated sodium hydrogencarbonate solution is added to the reaction mixture at 0° C. till pH=7 and the mixture is extracted with ethyl acetate. The aqueous phase is cooled, acidified with acetic acid and extracted twice with ethyl acetate. The organic phase is dried and evaporated. The residue is taken up twice with toluene and evaporated under vacuum without heating, yielding 0.11 g (57%) of (E)-5-[1-phenyl-2-(imidazol-1-yl)ethylidene]aminoxypentanoic acid.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. temperatureThe aqueous phase is cooled
  3. extractionextracted twice with ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated
  6. customevaporated under vacuum
  7. temperaturewithout heating

Sources & evidence

ORD record
ord-f3757ea4676a4497bf070aeb8929d28f
Source dataset
uspto-grants-1994_01
Patent number
US05280033

Reaction notes

Loading…