Methyl iodide → N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1699661Notes

Reaction equation

HRID 1699661 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]1.[C:27](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:14])(=[O:15])[N:10]([CH3:27])[CH2:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9908135N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 9865662N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (200 mg, 0.52 mmol), powdered potassium carbonate (85 mg, 0.62 mmol) and methyl iodide (88 mg, 0.62 mmol) were stirred under nitrogen in dry DMF (1 mL) for 24 hours. After evaporation of the solvent, the residue is partitioned between chloroform (65 mL) and water (15 mL). The chloroform is dried (MgSO4), filtered and evaporated. The residue is chromatographed over silica gel, eluting with 2-6% methanol-chloroform. The product is obtained as a white foam (156 mg, 75%). HRMS (FAB) calc'd for M+H=400.1342; Found: 400.1343.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is partitioned between chloroform (65 mL) and water (15 mL)
  3. dry with materialThe chloroform is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is chromatographed over silica gel
  7. washeluting with 2-6% methanol-chloroform

Sources & evidence

ORD record
ord-3568da6edd444acb8de3d5cb0103fc86
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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