Réaction #172573

Équation de réaction

ethyl 2-hydroxybenzoate

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

EDCI

dimethylaminopyridine

→

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

Rendement 96.7%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source