Reaktion #8241

Reaktionsgleichung

5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid yl)phenyl]oxazolidin-2-one

pyridine

→

ethyl acetate isohexane

Ausbeute 60.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction mixture was washed with water and brine
2. 2
   Trocknendried over sodium sulfate
3. 3
   Sonstigeevaporated to a gum

Vorschrift

To a stirred solution of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid yl)phenyl]oxazolidin-2-one (228 mg, 0.4 mM) in dry dichloromethane (5 ml) at 0–4° C., was added pyridine (158 mg, 2.0 mM) followed by dropwise addition of a solution of (S)-(+)-2,3,0-isopropylideneglycinoyl chloride (EP 0 413 401 A2; 200 mg, 1.2 mM) in dichloromethane (1 ml). The solution was stirred at 0–4° C. for 10 min. and then allowed to warm to ambient temperature. The reaction mixture was washed with water and brine, dried over sodium sulfate and evaporated to a gum. The title compound was isolated by MPLC (60% ethyl acetate/isohexane) and was obtained as a crisp foam on evaporation (158 mg, 60%).

Quelle