Reaktion #172573

Reaktionsgleichung

ethyl 2-hydroxybenzoate

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

EDCI

dimethylaminopyridine

→

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

Ausbeute 96.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle