Reacción #51869

Ecuación de reacción

diethyl 1,3,5-benzenetricarboxylate

O-benzylhydroxyamine hydrochloride

N-methylmorpholine

EDC

→

white powder

Rendimiento 59.0%

diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate

Rendimiento 59.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed by evaporator
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (150 mL)
3. 3
   LavadoThe organic solution was washed with 1 N HCL (150 mL)
4. 4
   Lavadowashed with saturated aqueous NaHCO3 (50 mL)
5. 5
   Secadodried over Na2SO4
6. 6
   Concentraciónconcentrated
7. 7
   Otroto give white solid
8. 8
   OtroThis material was recrystallized from EtOAc

Procedimiento

To a solution of diethyl 1,3,5-benzenetricarboxylate (3.192 g, 20 mol) and O-benzylhydroxyamine hydrochloride (4.789 g, 19 mmol) in 40 mL were added N-methylmorpholine (2.2 mL, 20 mmol) and EDC (3.834 g, 20 mmol) at 0° C., and the mixture was stirred at room temperature for 20 hours. The solvent was removed by evaporator and the residue was dissolved in EtOAc (150 mL). The organic solution was washed with 1 N HCL (150 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over Na2SO4, and concentrated to give white solid. This material was recrystallized from EtOAc to give 4.154 g of white powder (59% yield).

Fuente