反応 #366240

反応方程式

ethyl dithioacetate

sodium fluoride

(S)-(−)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone

potassium hydroxide

ethyl dithioacetate

sodium fluoride

potassium hydroxide

→

title compound

(S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

溶媒

ethanol

ethanol

ethanol

methylene chloride

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   洗浄washed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL)
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The crude product was recrystallized from methylene chloride/diethyl ether

実験手順

A solution of ethyl dithioacetate (100 mL, 0.876 mmol) and sodium fluoride (37 mg, 0.876 mmol) in ethanol (8.8 mL) under a nitrogen atmosphere was treated with a mixture of (S)-(−)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone, as prepared in Step 1, (300 mg, 0.876 mmol) and aqueous potassium hydroxide (1 M, 0.88 mL) in ethanol (43.8 mL). The resulting mixture was stirred at ambient temperature for 26 hours, during which additional ethyl dithioacetate (50 mL, 0.438 mmol), sodium fluoride (19 mg, 0.438 mmol), aqueous potassium hydroxide (1M, 0.44 mL) and ethanol (3.0 mL) was added, and was then diluted with methylene chloride (150 mL), washed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was recrystallized from methylene chloride/diethyl ether to give the title compound, mp 186-187° C. (dec.).

出典