Reacción #217690

Ecuación de reacción

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

Rendimiento 60.3%

Disolventes

N,N-dimethylformamide

diethyl ether

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente