Reaktion #422204

ord-fd3edf4107134009a5c1b713e6ebf0f3

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 94.0%

Edukte

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

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturheated to reflux
  2. 2
    Temperaturat reflux
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated
  5. 5
    SonstigeThe residue is chromatographed over silica

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08883832B2uspto-grants-2014_11