Reaktion #557095

Reaktionsgleichung

Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-methylsulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

cesium carbonate

1H-1,2,4-triazole-3-thiol

sodium triacetoxyborohydride

→

title compound

Ausbeute 16.5%

Di-tert-butyl (1R,2R,3R,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate

Ausbeute 16.5%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled
2. 2
   Sonstigequenched with water and aqueous NH4Cl
3. 3
   SonstigeThe mixture is transferred to a separatory funnel
4. 4
   Extraktionextracted with diethyl ether
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigeto give a residue
9. 9
   SonstigeThe residue is purified by flash chromatography (0 to 50% ethyl acetate/hexanes)

Vorschrift

Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-methylsulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (5.3 g, 8.21 mmol) is dissolved in dimethylformamide (100 mL). To this mixture is added cesium carbonate (5.40 g, 16.41 mmol), 1H-1,2,4-triazole-3-thiol (3.42 g, 32.83 mmol), and sodium triacetoxyborohydride (906 mg, 4.10 mmol). The mixture is stirred at 40° C. for 72 hours. The reaction is cooled and quenched with water and aqueous NH4Cl. The mixture is transferred to a separatory funnel and extracted with diethyl ether, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (0 to 50% ethyl acetate/hexanes) to give the title compound (0.88 g, 1.35 mmol, 16.5% yield). MS (m/z): 651 (M+H).

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