تفاعل #172573

معادلة التفاعل

ethyl 2-hydroxybenzoate

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

EDCI

dimethylaminopyridine

→

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

المردود 96.7%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر