تفاعل #2468029

معادلة التفاعل

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-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

المردود 60.3%

المذيبات

N,N-dimethylformamide

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.WAITfor 20 hours at 35° C
2. 2
   workup.STIRRINGthe mixture was stirred for 18 hours at 35° C
3. 3
   غسيلthe mixture was washed twice with water
4. 4
   تجفيفThe organic layers were dried over anhydrous sodium sulfate
5. 5
   ترشيحAfter the desiccant was filtered off
6. 6
   تركيزthe filtrate was concentrated under reduced pressure
7. 7
   أخرىThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent:hexane-ethyl acetate=5:1)

الإجراء التجريبي

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. 104 mg of sodium azide was further added thereto, and the mixture was stirred for 18 hours at 35° C. After being diluted with 50 mL of diethyl ether, the mixture was washed twice with water and then with a saturated aqueous solution of sodium chloride. The organic layers were 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:hexane-ethyl acetate=5:1), thereby yielding 775 mg of (1R,2R,3R,5R,6R)-3-azido-2-t-butoxycarbonylamino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

المصدر