Hydroxylamine → tert-Butyl 1-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenyl)ethylcarbamate

HRID 1961453Notes

Reaction equation

HRID 1961453 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[CH:7][CH:6]=1)=O.[NH2:23][OH:24]>N1C=CC=CC=1.CCO>[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[CH:7][CH:6]=1)=[N:23][OH:24]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 68071560tert-Butyl 1-(4-(2,2,2-trifluoroacetyl)phenyl)ethylcarbamate

Product 1

HCID 86661977tert-Butyl 1-(4-(2,2,2-trifluoro-1-(hydroxyimino)ethyl)phenyl)ethylcarbamateYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 1-(4-(2,2,2-trifluoroacetyl)phenyl)ethylcarbamate (1.02 g, 3.21 mmol) was mixed with NH2OH*HCl (223 mg, 3.21 mmol) in pyridine (25 ml) and EtOH (12 ml). The mixture was stirred at 80° C. for 16 hours and then evaporated. The residue was dissolved in EtOAc (60 ml), washed with H2O (2*40 ml), dried over MgSO4, filtered and evaporated. The product was purified by flash chromatography using CH2Cl2/MeOH (20:0→20:1) as eluent to give 640 mg (60%) of the title compound as pale solids.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in EtOAc (60 ml)
  3. washwashed with H2O (2*40 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-ad4b72bc8a9b426089741fd6b7eedc03
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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