تفاعل #8238

معادلة التفاعل

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

5(R)-hydroxymethyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

tributylphosphine

1,1-(azodicarbonyl)dipiperidine

→

oil

5(S)-Isoxazol-3-ylaminomethyl-3-(3-fluoro-4-morpholinophenyl)-oxazolidin-2-one

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىhad formed
2. 2
   ترشيحThe reaction mixture was filtered
3. 3
   غسيلthe residue washed with tetrahydrofuran
4. 4
   تركيزThe filtrate was concentrated by rotary evaporation

الإجراء التجريبي

To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (260 mg, 1.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (see WO 95/07271; 293 mg, 1 mmol) and tributylphosphine (303 mg, 1.5 mmol) in dry tetrahydrofuran (10 ml) at 0° C. under a nitrogen atmosphere, was added 1,1-(azodicarbonyl)dipiperidine (378.5 mg, 1.5 mmol) in dry tetrahydrofuran (3 ml). The reaction allowed to warm to room temperature and was stirred for 4 days by which time a white suspension had formed. The reaction mixture was filtered and the residue washed with tetrahydrofuran. The filtrate was concentrated by rotary evaporation to give a yellow oil (1.2 g) which was purified by MPLC (30% ethyl acetate/hexane, ICN Alumina N 32–63) and further MPLC (100% CH2Cl2, ICN Alumina N 32–63). Concentration of the fractions by rotary evaporation gave the title compound as a crisp white foam (296 mg, 55%).

المصدر