Reaktion #217694

Reaktionsgleichung

3,4-dichlorobenzoyl chloride

(1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

ethyl acetate

→

(1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzoyloxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Ausbeute 99.9%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthis ethyl acetate solution was washed with a saturated aqueous solution of copper sulfate and with water
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   FiltrationThe desiccant was filtered off
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=10:1)

Vorschrift

234 mg of 3,4-dichlorobenzoyl chloride was added to 202 mg of (1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester dissolved in 3.7 mL of pyridine, and the mixture was stirred for 28 hours at room temperature, under a nitrogen atmosphere. After 100 mL of ethyl acetate was added to the reaction solution, this ethyl acetate solution was washed with a saturated aqueous solution of copper sulfate and with water, and then 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, eluent: hexane-ethyl acetate=10:1), thereby yielding 298 mg of (1R,2R,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzoyloxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester.

Quelle