Methyl propiolate → (S)-N-[[3-[3-Fluoro-4-(4-carbomethoxy-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1955117Notes

Reaction equation

HRID 1955117 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].[C:22]([O:26][CH3:27])(=[O:25])[C:23]#[CH:24]>C1C=CC=CC=1>[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:24]=[C:23]([C:22]([O:26][CH3:27])=[O:25])[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 10708829(S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 10714593(S)-N-[[3-[3-Fluoro-4-(4-carbomethoxy-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 68.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution 1.0 g(3.4 mmol) of the azide of Example 17 in 50 mL benzene was treated with 573 mg(6.8 mmol) of methyl propiolate followed by warming at reflux for 24 h. The mixture was cooled and the product isolated by filtration of the reaction mixture. These procedures afforded 880 mg of the title compound as a white solid. High Resolution Mass Spectrum (EI): calcd for C16H16FN5O5 : 377.1135. found: 377.1131.

Workup

  1. temperatureby warming
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was cooled
  4. customthe product isolated by filtration of the reaction mixture

Sources & evidence

ORD record
ord-1e491d94781042f2840a1cee872ff5b8
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

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