(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → 2-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

HRID 1523713Notes

Reaction equation

HRID 1523713 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[N:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][C:26]2=[O:31])=[CH:21][CH:20]=1)=[C:17]=[O:18]>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:18]=[C:17]1[N:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C:26]3=[O:31])=[CH:21][CH:20]=2)[CH2:3][C@H:2]([CH2:4][N:5]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:15])[O:1]1

Participants

5

Reactant 2

HCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimideHCID 533414214-(4-Isocyanatophenyl)morpholin-3-one

Product 1

HCID 116903172-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dioneYield 90%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

(S)-2-(oxiran-2-ylmethy)isoindoline-1,3-dione (3.87 g, 19.06 mmol, 1.1 eq.) and 4-(4-isocyanatophenyl)morpholin-3-one (3.77 g, 17.29 mmol) were dissolved in acetonitrile (70 mL) respectively, then heated to reflux. Tetra-n-butylammonium bromide (0.55 g, 1.71 mmol) was added, the mixture was reacted for 4 h, white solid was obtained by filtration (6.57 g, yield: 90.0%).

Workup

  1. temperatureheated to reflux
  2. customthe mixture was reacted for 4 h
  3. customwhite solid was obtained by filtration (6.57 g, yield: 90.0%)

Sources & evidence

ORD record
ord-128d206e843f4685ab777eda8bb17e87
Source dataset
uspto-grants-2015_07
Patent number
US09079892B2

Reaction notes

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