Reacción #172573

Ecuación de reacción

ethyl 2-hydroxybenzoate

2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid

EDCI

dimethylaminopyridine

→

ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate

Rendimiento 96.7%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between CH2Cl2 and brine
2. 2
   ExtracciónThe aqueous layer was extracted with CH2Cl2
3. 3
   Secadothe combined organic extracts were dried over MgSO4
4. 4
   OtroThe crude material was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Procedimiento

To a solution of ethyl 2-hydroxybenzoate (0.5 g, 3.0 mmol) in CH2Cl2 (8 mL) was added 2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (0.8 g, 3.0 mmol), EDCI (0.63 g, 3.3 mmol) and dimethylaminopyridine (0.037 g, 0.3 mmol). The reaction was stirred (RT, 3 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4. The crude material was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to afford ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate (1.2 g). Mass calculated for C235H27NO6=413.46; found: [M+Na]+=437.1.

Fuente