Acetic Acid → Compound 3

HRID 747213Notes

Reaction equation

HRID 747213 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 acetate

Product 1

HCID 20788885Compound 3Yield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester (30 g, 79 mM) was treated with potassium carbonate (16.4 g, 0.119 mM) 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-065f4aad6bef4bcc8f0c1020c8fa2b1c
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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