Réaction #531903

Équation de réaction

4-((t-butoxycarbonylamino)methyl)benzoic acid

o-phenylene diamine

EDCI

HOBt

→

compound

Rendement 56.0%

t-butyl-4-(2-aminophenylcarbamoyl)benzylcarbamate

Rendement 56.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGwas stirred at room temperature overnight
2. 2
   AutreSubsequently, the reaction mixture was evaporated to half its volume
3. 3
   workup.DISSOLUTIONthe resulting solution was dissolved in ethyl acetate
4. 4
   Lavagewashed successively with saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL)
5. 5
   SéchageThe organic layer was dried over Na2SO4
6. 6
   Concentrationconcentrated

Mode opératoire

To a suspension of 4-((t-butoxycarbonylamino)methyl)benzoic acid (6.08 g, 24.2 mmol) in DMF was added o-phenylene diamine (2.9 g, 29 mmol), EDCI (9.3 g, 48.4 mmol) and HOBt (3.8 g, 24.2 mmol). TEA (11.8 mL, 84.8 mmol) was added drop wise with constant stirring to the above reaction mixture, which was stirred at room temperature overnight. Subsequently, the reaction mixture was evaporated to half its volume; the resulting solution was dissolved in ethyl acetate, washed successively with saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the pure compound (4.6 g, 56% yield).

Source