Propargyl alcohol → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1782085Notes

Reaction equation

HRID 1782085 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]=[N+:16]=[N-:17])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8].[CH2:19]([OH:22])[C:20]#[CH:21]>C(#N)C.[Cu]I>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:21]=[C:20]([CH2:19][OH:22])[N:17]=[N:16]3)[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 58822464(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (10 g, 28 mmol) and propargyl alcohol (3.2 mL, 56 mmol) in acetonitrile (80 mL) was treated with CuI (526 mg, 2.8 mmol) and then stirred overnight. The solidified reaction mixture was extracted with ethyl acetate:acetonitrile, washed with water, and dried over magnesium sulfate, and then evaporated under reduced pressure to give a crude product sufficiently pure for further use (12.3 g, quantitative).

Workup

  1. customThe solidified reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washacetonitrile, washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6eb85ba576714ed78d7c0c2108d5cfa0
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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