Reaction #88318

ord-a9aebef428104f8f943fcab898049502

Reaction equation

O=C([O-])[O-].[K+].[K+]
Potassium carbonate
CC(N)=NO
acetamide oxime
CCOC(=O)C(Cc1ccccc1)C(=O)N[C@@H](Cc1ccc([N+](=O)[O-])cc1)c1nc(CC)cs1
Ethyl 2-benzyl-3-((S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino)-3-oxopropanoate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(N)=NO
acetamide oxime
→
CCc1csc([C@H](Cc2ccc([N+](=O)[O-])cc2)NC(=O)C(Cc2ccccc2)c2nc(C)no2)n1
desired product
Yield 94.0%
CCc1csc([C@H](Cc2ccc([N+](=O)[O-])cc2)NC(=O)C(Cc2ccccc2)c2nc(C)no2)n1
N—[(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenylpropanamide
Yield 94.0%

Reactants

O=C([O-])[O-].[K+].[K+]
Potassium carbonate
CC(N)=NO
acetamide oxime
CCOC(=O)C(Cc1ccccc1)C(=O)N[C@@H](Cc1ccc([N+](=O)[O-])cc1)c1nc(CC)cs1
Ethyl 2-benzyl-3-((S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino)-3-oxopropanoate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(N)=NO
acetamide oxime

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureheated to reflux
  2. 2
    Temperatureat reflux
  3. 3
    Filtrationfiltered
  4. 4
    Concentrationconcentrated
  5. 5
    OtherThe residue is chromatographed over silica

Procedure

Ethyl 2-benzyl-3-((S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino)-3-oxopropanoate is dissolved in toluene (5 mL) and heated to reflux. Potassium carbonate (80 mg) and acetamide oxime (43 mg) are added. and treated with 80 mg potassium carbonate and 43 mg acetamide oxime at reflux. The reaction mixture is cooled to room temperature, filtered and concentrated. The residue is chromatographed over silica to afford 0.221 g (94%) of the desired product as a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09440963B2uspto-grants-2016_09