Dimethylformamide → N-((3-(3-Fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)phthalimide, (S)-

HRID 969707Notes

Reaction equation

HRID 969707 reaction equation
Cl[CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:4]1.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K].CN(C)C=O>O>[F:21][C:11]1[CH:10]=[C:9]([N:5]2[CH2:4][C@H:3]([CH2:2][N:26]3[C:25](=[O:27])[C:24]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]4[C:22]3=[O:32])[O:7][C:6]2=[O:8])[CH:14]=[CH:13][C:12]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 461769455-(Chloromethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, (R)-

Product 1

HCID 12973056N-((3-(3-Fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)phthalimide, (S)-Yield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone (60 g), potassium phthalimide (40 g) and Dimethyl formamide (400 ml) is heated for 5 hours at reflux temperature. The reaction mixture is cooled to ambient temperature, poured in to 2 L water and filtered the solid to give 50 gm (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide.

Workup

  1. temperatureis heated for 5 hours
  2. temperatureat reflux temperature
  3. filtrationfiltered the solid

Sources & evidence

ORD record
ord-52880e842a2349878c87c64a3283a2c4
Source dataset
uspto-grants-2007_12
Patent number
US07307163B2

Reaction notes

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