Réaction #5338

Équation de réaction

crude crystals

Methyl 2-ethoxy-1-[[2'-(ethoxycarbonyloxy-carbamimidoyl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

1,8-diazabicyclo[5.4.0]undec-7-ene

→

title compound

Rendement 57.6%

Methyl 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

Rendement 57.6%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml)
2. 2
   LavageThe organic layer was washed with water
3. 3
   Autredried
4. 4
   Concentrationconcentrated to dryness
5. 5
   AutreThe residue was crystallized from chloroformethyl acetate

Mode opératoire

The crude crystals (4.0 g) obtained in Example (57b) was dissolved in ethyl acetate (50 ml). To the solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 3.2 g), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was partitioned between ethyl acetate (50 ml) and 1N HCl (20 ml). The organic layer was washed with water, dried and concentrated to dryness. The residue was crystallized from chloroformethyl acetate to afford the title compound as colorless prisms (2.1 g, 45%), which was in agreement with that obtained in Example (1d).

Source