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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 345631Erstellt: 26. Oktober 2026

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

https://huagongshe.com/reaction/345631

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPhosphateHCID 1061—
EduktPenicillin GHCID 5904—
EduktPotassium HydroxideHCID 14797—
EduktMethyl phenoxyacetateHCID 16365—
Edukt2-[2-(2-Furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate saltHCID 86745171—
LösungsmittelWaterHCID 962—
Produkt(2R,3S)-3-Phenoxyacetylamino-2-[(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl esterHCID 988646613%

Reaktionsbedingungen

Temperatur28 °C

Reaktionsschritte

A 100 mg sample of [(2R,3S),(2S,3R)]-3-amino- <2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate salt and a 135 mg sample of methyl phenoxyacetate were added to 0.lM phosphate buffer (100 ml final volume) and adjusted to pH=6.0 with lN KOH. Milli-Q™ H2O washed Sclavo penicillin G amidase (40 I.U. of enzyme per gram of substrate) was then added to the reaction mixture and the pH of reaction mixture was maintained at 6.0 and temperature at 28° C. for 8 hours. The reaction mixture was then filtered to remove the immobilized enzyme and extracted two times with ethyl acetate. The organic extracts were then dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The title compound was then isolated by column chromatography from this residue using a Kiesegel 60™ column eluted with toluene/ethyl acetate (70/30). Yield: 13%.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05057607
Quelldatensatzuspto-grants-1991_10
ORD IDord-678c2905b4724c37ac1f44b76fa1f741
Quellennotizuspto-grants-1991_10