Pyridine → HCID 68700839, compound

HRID 750903Notes

Reaction equation

HRID 750903 reaction equation
[CH3:1][O:2][C:3]1([O:24][CH3:25])[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][CH:10]=2)[CH2:5][CH:4]1[F:23].[N:26]1C=CC=[CH:28][CH:27]=1.C(OC(=O)C)(=[O:34])C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1([O:24][CH3:25])[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][CH2:28][C:27]([NH2:26])=[O:34])[O:17][C:16]3=[O:22])=[CH:13][CH:14]=2)[CH2:5][CH:4]1[F:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69315286HCID 69315286, compound

Product 1

HCID 68700839HCID 68700839, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (S)-{3-[4-(4,4-dimethoxy-3-fluoropiperidin-1-yl)-phenyl]-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 49% 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-7ba3d681935e464a9fdbac8bcc2ca458
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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