Acetic Acid → Compound 3

HRID 459007Notes

Reaction equation

HRID 459007 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][O:15]C(=O)C)[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[I:8].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.O>CO.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 20788911[(5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetate2×

Product 1

HCID 20788885Compound 3Yield 86.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester (Intermediate 2, 30 g, 79 mmol) was treated with potassium carbonate (16.4 g, 0.119 mmol) in a mixture of methanol (800 ml) and dichloromethane (240 ml) at ambient temperature for 25 minutes, then immediately neutralised by the addition of acetic acid (10 ml) and water (500 ml). The precipitate was filtered, washed with water, and dissolved in dichloromethane (1.2 L), the solution washed with saturated sodium bicarbonate, and dried (magnesium sulfate). Filtration and evaporation gave the desired product (23 g).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. dissolutiondissolved in dichloromethane (1.2 L)
  4. washthe solution washed with saturated sodium bicarbonate
  5. dry with materialdried (magnesium sulfate)
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-bff60960af6f456c820253387b07c07e
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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