반응 #172573

반응 방정식

ethyl 2-hydroxybenzoate

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

EDCI

dimethylaminopyridine

→

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

수율 96.7%

용매

CH2Cl2

반응 조건

후처리

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

실험 절차

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.

출처