Reaktion #432812

Reaktionsgleichung

3-amino-2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate

methyl phenylacetate

potassium phosphate

penicillin G

→

title compound

Ausbeute 42.2%

(2R,3S)-3-Phenylacetylamino-2-[(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester

Ausbeute 42.2%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction mixture was then extracted two times with ethyl acetate
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   SonstigeThe ethyl acetate portion was evaporated to dryness in vacuo
4. 4
   Sonstigethe residue was purified by column chromatography
5. 5
   Wascheneluted with toluene/ethyl acetate (50/50)

Vorschrift

A 100 mg sample of cis(racemic at 2 and 3 position) 3-amino-2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate and 121 mg of methyl phenylacetate was added to 0.1 M potassium phosphate buffer(100ml) at pH=6.0, and the temperature maintained at 28° C. Milli-Q™ H2O washed Sclavo penicillin G amidase (0.035 I.U./%mole of substrate; 0.100 I.U./mg of substrate) was added and the reaction allowed to proceed overnight. The reaction mixture was then extracted two times with ethyl acetate and dried over anhydrous sodium sulfate. The ethyl acetate portion was evaporated to dryness in vacuo and the residue was purified by column chromatography using a Kiesegel 60™ column eluted with toluene/ethyl acetate (50/50), to obtain 45.7 mg (42.2% yield) of the title compound.

Quelle