Ammonium Hydroxide → (5R)-(-)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([C:14](OC)=[O:15])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8].[OH-].[NH4+:20]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([C:14]([NH2:20])=[O:15])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8]Participants
Procedure
A solution of (−)-methyl (5R)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxylate (Step 2, 6.23 g, 17.1 mmol) in acetonitrile (85 mL) was treated with concentrated ammonium hydroxide (85 mL), and the resulting mixture was stirred at ambient temperature for 1 hour. The mixture was then diluted with saline (100 mL) and extracted with methylene chloride (3×100 mL), and the combined organic phase was washed with saline (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was diluted with hot ethyl acetate (200 mL) and filtered to remove inorganic residue, and the filtrate was diluted with hexanes (300 mL). The resulting precipitate was isolated by filtration to give the title compound, mp 176-178° C.; MS (ESI+) for C10H8FIN2O3 m/z 351 (M+H)+; [α]25D=−19 (c 0.97, DMSO).
Workup
- additionThe mixture was then diluted with saline (100 mL)
- extractionextracted with methylene chloride (3×100 mL)
- washthe combined organic phase was washed with saline (100 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- additionThe crude product was diluted with hot ethyl acetate (200 mL)
- filtrationfiltered
- customto remove inorganic residue
- additionthe filtrate was diluted with hexanes (300 mL)
- customThe resulting precipitate was isolated by filtration
Sources & evidence
- ORD record
- ord-15f755a8f5bb475d8104597d3f89f6d9
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049443B2
Reaction notes
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