Reacción #432812

Ecuación de reacción

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

methyl phenylacetate

potassium phosphate

penicillin G

→

title compound

Rendimiento 42.2%

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

Rendimiento 42.2%

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe reaction mixture was then extracted two times with ethyl acetate
2. 2
   Secadodried over anhydrous sodium sulfate
3. 3
   OtroThe ethyl acetate portion was evaporated to dryness in vacuo
4. 4
   Otrothe residue was purified by column chromatography
5. 5
   Lavadoeluted with toluene/ethyl acetate (50/50)

Procedimiento

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.

Fuente