Реакция #2334200

Уравнение реакции

lithio(trimethylsilyl)acetylene

(S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

potassium carbonate

ammonium chloride

→

title compound

Выход 19.0%

(S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Выход 19.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеto come to room temperature
2. 2
   workup.STIRRINGfurther stirred for 18 hours
3. 3
   Экстракцияthe reaction mixture was extracted with ethyl acetate (3×40 ml)
4. 4
   ДругоеThe removal of the solvent
5. 5
   Другоеprovided a residue, which
6. 6
   ДругоеThe solvent was removed
7. 7
   Другоеthe residual mass was purified by column chromatography over silica gel

Методика

A mixture of lithio(trimethylsilyl)acetylene (1.72 mmol) and (S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.72 mmol) in tetrahydrofuran (10 ml) was stirred at a temperature −78° C. for 15 minutes. It was allowed to come to room temperature and further stirred for 18 hours. The reaction mixture was then stirred with aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate (3×40 ml). The removal of the solvent provided a residue, which was stirred in aqueous methanolic (15 ml) solution of potassium carbonate (1.72 mmol) for 3 hours. The solvent was removed and the residual mass was purified by column chromatography over silica gel to provide title compound in 19% yield. M.P. 166-167° C. and MS (M+1)=376 (MH+, 100%) M.F.=C19H22FN3O4.

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