Reaction #51869

Reaction equation

diethyl 1,3,5-benzenetricarboxylate

O-benzylhydroxyamine hydrochloride

N-methylmorpholine

EDC

→

white powder

Yield 59.0%

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

Yield 59.0%

Conditions

Workup

1. 1
   OtherThe solvent was removed by evaporator
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (150 mL)
3. 3
   WashThe organic solution was washed with 1 N HCL (150 mL)
4. 4
   Washwashed with saturated aqueous NaHCO3 (50 mL)
5. 5
   Dryingdried over Na2SO4
6. 6
   Concentrationconcentrated
7. 7
   Otherto give white solid
8. 8
   OtherThis material was recrystallized from EtOAc

Procedure

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).

Source