Potassium Carbonate → (S)-N-[[3-[3-Fluoro-4-(4-(1-hydroxyiminomethyl)--1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1415902Notes

Reaction equation

HRID 1415902 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])=[CH:6][C:5]=1[F:21])=[N+:2]=[N-:3].Cl.[NH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+].[CH2:31]1[CH2:35]OC[CH2:32]1.CO>>[F:21][C:5]1[CH:6]=[C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])[CH:8]=[CH:9][C:4]=1[N:1]1[CH:32]=[C:31]([CH:35]=[N:23][OH:24])[N:3]=[N:2]1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10708829(S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 53703125(S)-N-[[3-[3-Fluoro-4-(4-(1-hydroxyiminomethyl)--1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 20%

Procedure

A solution of 150 mg (0.40 mmol) of the compound of Example 17 in 10 mL of 1:1 THF-methanol was treated with 66 mg (0.96 mmol) of hydroxylamine hydrochloride and 66 mg (0.48 mmol) of potassium carbonate, followed by stirring at ambient temperature for 8 h, and then warming at reflux for 2 h. The mixture was concentrated in vacuo, and the residue was subjected to radial chromatography on a 2 mm chromatotron plate, eluting with 5% (v/v) methanol in dichloromethane. These procedures afforded 30 mg (20%) of the title compound as a white solid. MassSpectrum (EI): m/z 376, 332, 318, 287, 274, 245, 220, 202, 187, 175, 163, 149, 139, 82, 56.

Workup

  1. temperaturewarming
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. washeluting with 5% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-aa3b7e78be0a4219828c8e557c7bf5d4
Source dataset
uspto-grants-1999_06
Patent number
US05910504

Reaction notes

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