反応 #8264

反応方程式

3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

→

desired product

収率 48.6%

3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

収率 48.6%

溶媒

acetic acid

water

反応条件

後処理

1. 1
   ろ過The mixture was filtered through celite
2. 2
   その他the residue after evaporation
3. 3
   その他partitioned between ethyl acetate (10 ml) and aqueous sodium bicarbonate (15 ml)
4. 4
   洗浄The organic phase was washed with sodium bicarbonate (2×15 ml), water (15 ml)
5. 5
   乾燥dried (magnesium sulfate)
6. 6
   その他evaporated
7. 7
   その他The crude product was purified by chromatography on a 10 g Biotage silica column
8. 8
   洗浄eluting with a gradient from dichloromethane to ethyl acetate

実験手順

3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (400 mg, 0.5 mM) was stirred in a mixture of acetic acid (10 ml) and water (2 ml). Zinc dust (203 mg, 3.1 mM) was added, and the mixture stirred 30 minutes at ambient temperature. The mixture was filtered through celite, and the residue after evaporation partitioned between ethyl acetate (10 ml) and aqueous sodium bicarbonate (15 ml). The organic phase was washed with sodium bicarbonate (2×15 ml), water (15 ml), dried (magnesium sulfate), and evaporated. The crude product was purified by chromatography on a 10 g Biotage silica column, eluting with a gradient from dichloromethane to ethyl acetate. Relevant fractions were combined to give the desired product (141 mg).

出典