P-Anisidine → 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one

HRID 898828Notes

Reaction equation

HRID 898828 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.FC(F)(F)S(O)(=O)=O.[C:18]([N:23]1[CH2:27][CH2:26][O:25][C:24]1=[O:28])(=[O:22])/[CH:19]=[CH:20]/[CH3:21].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:20]([CH3:21])[CH2:19][C:18]([N:23]2[CH2:27][CH2:26][O:25][C:24]2=[O:28])=[O:22])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 25517Ammonium ChlorideHCID 62406Trifluoromethanesulfonic acidHCID 5365845HCID 5365845, compound

Product 1

HCID 121794903-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of anisidine (55.4 mg, 0.45 mmol) in toluene (1.5 ml) was cooled to 0° C., and trifluoromethanesulfonic acid (40 μL, 0.45 mmol) was added dropwise. The mixture was stirred for 10 minutes, and to this solution were added Pd((R)-binap)(OH2)2(OTf)2 (8 mg, 0.00752 mmol) and 3-crotonoyl-1,3-oxazolidin-2-one (47 mg, 0.3 mmol). The ice-cooling bath was removed and the mixture was reacted at room temperature for 20 hours. A saturated aqueous solution of ammonium chloride was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give the objective 3-[3-(4-methoxyphenylamino)butyryl]-1,3-oxazolidin-2-one (66.5 mg, 96% yield). The enantiomeric excess was determined by a liquid chromatography with an optical isomer separating column (column: AD-H) to be 94% e.e.

Workup

  1. customwas removed
  2. customthe mixture was reacted at room temperature for 20 hours
  3. customto quench
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated
  7. custompurified by a silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8783b8e3be85477694f5e7989f1c23c1
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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