反应详情

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. Asaturated 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-butoxycarbonylamino3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

1. temperaturecooling
2. extractionthe mixture was extracted five times with chloroform
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationAfter the desiccant was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe 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)