반응 #8240

반응 방정식

3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole

5(R)-hydroxymethyl-3-(3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one

tributylphosphine

1,1′-(azodicarbonyl)dipiperidine

→

title compound

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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to come to room temperature
2. 2
   workup.STIRRINGit was then stirred for 2 days
3. 3
   여과The mixture was filtered
4. 4
   농축concentrated by rotary evaporation
5. 5
   기타chromatographed by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32–63)
6. 6
   기타triturated with ether

실험 절차

To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (1.30 g, 5.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one (WO 97/30995; 1.91 g, 5.0 mmol) and tributylphosphine (1.52 g, 7.5 mmol) in dry tetrahydrofuran (50 ml) under a nitrogen atmosphere at 0° C., was added 1,1′-(azodicarbonyl)dipiperidine (1.89 g, 7.5 mmol) in dry tetrahydrofuran (15 ml). The solution was stirred at 0° C. for 30 minutes before being allowed to come to room temperature and it was then stirred for 2 days. The mixture was filtered, concentrated by rotary evaporation and chromatographed by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32–63), and triturated with ether to give the title compound as a white amorphous solid (1.62 g, 52%).

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