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) is treated with concentrated ammonium hydroxide (85 mL), and the resulting mixture is stirred at ambient temperature for 1 h. The mixture is then diluted with saline (100 mL) and extracted with methylene chloride (3×100 mL), and the combined organic phase is washed with saline (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product is diluted with hot ethyl acetate (200 mL) and filtered to remove inorganic residue, and the filtrate is diluted with hexanes (300 mL). The resulting precipitate is 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 is then diluted with saline (100 mL)
- extractionextracted with methylene chloride (3×100 mL)
- washthe combined organic phase is washed with saline (100 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- additionThe crude product is diluted with hot ethyl acetate (200 mL)
- filtrationfiltered
- customto remove inorganic residue
- additionthe filtrate is diluted with hexanes (300 mL)
- customThe resulting precipitate is isolated by filtration
Sources & evidence
- ORD record
- ord-548313649d6848cb9015d8504b49c500
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645781B2
Reaction notes
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