Methyl iodide → (4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

HRID 1599131Notes

Reaction equation

HRID 1599131 reaction equation
[CH3:1][C@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].[CH3:25]I>O1CCCC1.C(OCC)(=O)C>[CH3:1][C@H:2]1[C@H:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:24])[C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:25]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 57297643(4S,5S)-4-methyl5-Phenyl-3-(2-methoxyphenylacetyl)-2-oxazolidinone

Product 1

HCID 54310187(4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

19.1 g of sodium 1,1,1,3,3,3-hexamethyldisilazanate are added to a solution, cooled to -50° C., of 10 g of (4S,5S)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]oxazolidin-2-one in 150 cm3 of tetrahydrofuran, the mixture is stirred at this temperature for 45 minutes, and then 7.72 cm3 of methyl iodide are added. The reaction mixture is subsequently stirred at room temperature for 15 hours, then diluted with ethyl acetate, washed with 50 cm3 of water followed by 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is recrystallized from isopropyl ether, drained and dried. 4.2 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]oxazolidin-2-one are obtained in the form of a white solid.

Workup

  1. stirringThe reaction mixture is subsequently stirred at room temperature for 15 hours
  2. washwashed with 50 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue obtained
  6. customis recrystallized from isopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-bc5c0cdc369d4dcc984d73212a5a317b
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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