Propargyl alcohol → HCID 10172554, compound

HRID 1268986Notes

Reaction equation

HRID 1268986 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N:18]([CH2:21][C@@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]3)=[C:30]([F:40])[CH:29]=2)[CH2:23]1)=[N+:19]=[N-:20]>C(O)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[F:40][C:30]1[CH:29]=[C:28]([N:24]2[CH2:23][C@H:22]([CH2:21][N:18]3[CH:3]=[C:2]([CH2:1][OH:4])[N:20]=[N:19]3)[O:26][C:25]2=[O:27])[CH:33]=[CH:32][C:31]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 23667548Sodium AscorbateHCID 58840977(5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one2×

Product 1

HCID 10172554HCID 10172554, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Propargyl alcohol (79 μl, 1.3 mmol), copper sulfate (37 μl of 0.30 M aqueous solution, 11 mmol), and sodium ascorbate (112 μl of 1.0 M aqueous solution, 0.11 mmol) were added to a solution of (5R)-5-(azidomethyl)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,3-oxazolidin-2-one (Intermediate 7) (0.355 g, 1.12 mmol) in ethanol (2 ml) and water (2 ml). The reaction mixture was allowed to stir at room temperature for 24 h. The aqueous phase was extracted three times with dichloromethane, the organic layers were combined and washed once with brine and dried over magnesium sulfate. Chromatography on silica gel with 10% to 14% methanol in dichloromethane gave 0.197 g. of the title compound.

Workup

  1. extractionThe aqueous phase was extracted three times with dichloromethane
  2. washwashed once with brine
  3. dry with materialdried over magnesium sulfate
  4. customChromatography on silica gel with 10% to 14% methanol in dichloromethane gave 0.197 g

Sources & evidence

ORD record
ord-665edd0a5ea245baa50dbe49617a4a99
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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