Acetic Acid → HCID 57271238, compound

HRID 1780967Notes

Reaction equation

HRID 1780967 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].CI.[C:27](O)(=O)C>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])[CH3:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 53666438HCID 53666438, compound

Product 1

HCID 57271238HCID 57271238, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution, cooled to -50° C., of 22.82 g of (4R, 5R)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]-2-oxazolidinone in 190 cm3 of tetrahydrofuran are added 19.31 g of sodium 1,1,1,3,3,3-hexamethyldisilazide, and the mixture is stirred for 45 minutes at this temperature, followed by addition of 8.82 cm3 of methyl iodide. The reaction mixture is subsequently stirred for 15 hours at room temperature, and then 18.65 cm3 of acetic acid are added, and the mixture is diluted with 200 cm3 of ethyl acetate and washed with 200 cm3 of water and then with 250 cm3 of saturated aqueous sodium chloride solution, and dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallized in isopropyl ether, filtered off and dried. 10.95 g of (4R, 5R)-4-methyl-5-phenyl-3-[(R)-2-(2-methoxyphenyl)propionyl]-2-oxazolidinone are obtained, in the form of a white solid melting at 110° C.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 15 hours at room temperature
  2. washwashed with 200 cm3 of water
  3. dry with materialwith 250 cm3 of saturated aqueous sodium chloride solution, and dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue obtained
  6. customis crystallized in isopropyl ether
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-4bd13a1ef22b4a92a19593e562a1264a
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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