تفاعل #2468030

معادلة التفاعل

sodium chloride

pyridine

3,4-dichlorobenzylbromide

(1R,2R,3R,5R,6R)-3-amino-2-t-butoxycarbonylamino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

→

(1R,2R,3R,5R,6R)-2-t-butoxycarbonylamino-3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

المردود 39.3%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   استخلاصthe mixture was extracted five times with chloroform
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   ترشيحAfter the desiccant was filtered off
5. 5
   تركيزthe filtrate was concentrated under reduced pressure
6. 6
   أخرىThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent:chloroform-ethanol=100:1 to 50:1, followed by hexane-ethyl acetate=5:1)

الإجراء التجريبي

42 μL of pyridine and 123 mg of 3,4-dichlorobenzylbromide were added to 175 mg of (1R,2R,3R,5R,6R)-3-amino-2-t-butoxycarbonylamino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 0.88 mL of chloroform at ice-cooling, and the mixture was stirred for 3 days at room temperature. A saturated aqueous solution of sodium chloride was added thereto, and the mixture was extracted five times with chloroform. The organic layers were combined and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200, eluent:chloroform-ethanol=100:1 to 50:1, followed by hexane-ethyl acetate=5:1), thereby yielding 98 mg of (1R,2R,3R,5R,6R)-2-t-butoxycarbonylamino-3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

المصدر