Réaction #512062

ord-1585048517364a568b040bb233b1e28c

Équation de réaction

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
Rendement 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
Rendement 94.0%

Réactifs

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

Réactifs

Aucun

Solvants

Cc1ccccc1
toluene

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureheated to reflux
  2. 2
    Températureat reflux
  3. 3
    Filtrationfiltered
  4. 4
    Concentrationconcentrated
  5. 5
    AutreThe residue is chromatographed over silica

Mode opératoire

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.v1Brevet: US08106078B2uspto-grants-2012_01