Reaktion #2333288

Reaktionsgleichung

1-(cyclohexyloxycarbonyloxy)ethyl iodide

sodium (1R,5S,6S)-2-[[(Z)-2-[4-(2-hydroxyethoxy)methylthiazol-5-yl]ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

→

title compound

1-(Cyclohexyloxycarbonyloxy)ethyl (1R,5S,6S)-2-[[(Z)-2-[4-(2-hydroxyethoxy)methylthiazol-5-yl]ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Lösungsmittel

hexane

N,N-dimethylacetamide

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by separation into an upper layer
2. 2
   workup.ADDITIONBrine was added to the lower layer
3. 3
   Extraktionthe mixture was extracted twice with ethyl acetate
4. 4
   Waschenwere washed twice with brine
5. 5
   Trocknenwere dried over anhydrous magnesium sulfate
6. 6
   Filtrationwere filtered
7. 7
   Einengenwere concentrated under the reduced pressure
8. 8
   Sonstigethe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Vorschrift

A solution (2 ml) of 0.147 mg of 1-(cyclohexyloxycarbonyloxy)ethyl iodide in hexane was added to a solution of 51.8 mg of sodium (1R,5S,6S)-2-[[(Z)-2-[4-(2-hydroxyethoxy)methylthiazol-5-yl]ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 2 ml of N,N-dimethylacetamide under an argon atmosphere at −10° C. The mixture was stirred at the same temperature for one hr, and 2 ml of hexane was then added to the reaction solution, followed by separation into an upper layer and a lower layer. Brine was added to the lower layer, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed twice with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to give 61.7 mg of the title compound.

Quelle