반응 #217690

반응 방정식

sodium azide

(1R,2R,3S,5R,6R)-2-t-butoxycarbonylamino-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

sodium azide

→

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

수율 60.3%

용매

N,N-dimethylformamide

diethyl ether

반응 조건

후처리

1. 1
   workup.WAITfor 20 hours at 35° C
2. 2
   workup.STIRRINGthe mixture was stirred for 18 hours at 35° C
3. 3
   세척washed twice with water and with a saturated aqueous solution of sodium chloride
4. 4
   건조The organic layers were dried over anhydrous sodium sulfate
5. 5
   여과The desiccant was filtered off
6. 6
   농축the filtrate was concentrated under reduced pressure
7. 7
   기타The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=5:1)

실험 절차

313 mg of sodium azide was added to 1.63 g of (1R,2R,3S,5R,6R)-2-t-butoxycarbonylamino-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 16.3 mL of N,N-dimethylformamide, and the mixture was stirred for 1 hour at room temperature, and then for 20 hours at 35° C. After 104 mg of sodium azide was further added thereto, the mixture was stirred for 18 hours at 35° C. The mixture was diluted with 50 mL of diethyl ether, and then washed twice with water and with a saturated aqueous solution of sodium chloride. The organic layers were dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=5:1), thereby yielding 775 mg of (1R,2R,3R,5R,6R)-3-azido-2-t-butoxycarbonylamino-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

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