Acetic Anhydride → rac-Linezolid

HRID 1472497

Reaction equation

HRID 1472497 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH2:34])[O:30][C:29]2=[O:35])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44]>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][CH:31]([CH2:33][NH:34][C:43](=[O:45])[CH3:44])[O:30][C:29]2=[O:35])[CH:19]=[CH:20][C:21]=1[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 227145793-Fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one

Product 1

HCID 3929rac-LinezolidYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a reaction flask were added 6.53 mmol of dihydrochloride of 3-(3-fluoro-4-morpholinylphenyl-5-aminomethyl-1,3-oxazolidin-2-one (5a), 100 ml of dichloromethane and 2.95 ml (21.2 mmol) of triethylamine. Then 0.8 ml (8.45 mmol) of acetic anhydride was added while being stirred in an ice-bath. The mixture was then allowed to react at room temperature for 2 hours before being washed successively with 5% aqueous NaOH solution and saturated aqueous NaCl solution. The organic layer was then dried by anhydrous sodium sulfate and filtered, and subsequently put under reduced pressure for solvent removal. The residue was then subjected to recrystallization using ethyl acetate to give white needle crystals at a yield of 85%, HR-TOF-MS (+Q) m/z: 338.1520 (Calculated [C16H20FN3O4+H]+: 338.1516).

Workup

  1. customto react at room temperature for 2 hours
  2. washbefore being washed successively with 5% aqueous NaOH solution and saturated aqueous NaCl solution
  3. dry with materialThe organic layer was then dried by anhydrous sodium sulfate
  4. filtrationfiltered
  5. customsubsequently put under reduced pressure for solvent removal
  6. customThe residue was then subjected to recrystallization
  7. customto give white needle crystals at a yield of 85%, HR-TOF-MS (+Q) m/z

Sources & evidence

ORD record
ord-105550dc7a56445f8ca6182f96d8c40a
Source dataset
uspto-grants-2015_04
Patent number
US09012631B2

Linked notes

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