Pyridine → HCID 68698365, compound

HRID 750912Notes

Reaction equation

HRID 750912 reaction equation
[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20]N)[O:17][C:16]3=[O:22])=[CH:11][C:10]=2[F:23])[CH2:5][CH:4]1[F:24].[N:27]1C=CC=[CH:29][CH:28]=1.C(OC(=O)C)(=[O:35])C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1([O:25][CH3:26])[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][CH2:29][C:28]([NH2:27])=[O:35])[O:17][C:16]3=[O:22])=[CH:11][C:10]=2[F:23])[CH2:5][CH:4]1[F:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59753998HCID 59753998, compound

Product 1

HCID 68698365HCID 68698365, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (S)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-amine (6.73 mmol), pyridine (26.9 mmol), acetic anhydride (9.43 mmol) in ethyl acetate (25 ml) was stirred for 5 hours at room temperature. The reaction mixture was extracted with the ethyl acetate water mixture and combined organic layer was dried over sodium sulfate. The removal of the solvent afforded a residue, which was chromatographed over silica gel to give title compound in 58% yield.

Workup

  1. extractionThe reaction mixture was extracted with the ethyl acetate water mixture and combined organic layer
  2. dry with materialwas dried over sodium sulfate
  3. customThe removal of the solvent
  4. customafforded a residue, which
  5. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-dd1d5471cfe9439ea22b8147d92c12de
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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