Methyl iodide → (R)-4-[3-fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1804040Notes

Reaction equation

HRID 1804040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][OH:27])[CH2:24][O:23][C:22]3=[O:28])=[C:17]([F:29])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:33]I>CN(C)C=O.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:30])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][O:27][CH3:33])[CH2:24][O:23][C:22]3=[O:28])=[C:17]([F:29])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58484618(R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 54755121(R)-4-[3-fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl esterYield 56.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester (494 mg) described in Preparation Example 92 was dissolved in N,N-dimethylformamide (3.7 mL), sodium hydride (51 mg, 60% in oil) was added under ice-cooling and the mixture was stirred. Then, under ice-cooling, methyl iodide (182 mg) was added and the mixture was stirred at room temperature. The reaction mixture was added to saturated brine under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (290 mg).

Workup

  1. temperaturecooling
  2. temperatureThen, under ice-cooling
  3. stirringthe mixture was stirred at room temperature
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed twice with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-cc50a1867fde495b9ab1517c5e1eb1c2
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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