Lithium Bromide → 2-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione

HRID 1523710Notes

Reaction equation

HRID 1523710 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].[Br-].[Li+]>O1CCCC1>[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 3

HCID 82050Lithium BromideHCID 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 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-(oxiran-2-ylmethyl)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 tetrahydrofuran (70 mL) respectively and then heated to reflux. Then lithium bromide (0.15 g, 1.74 mmol) was added, the mixture was reacted for 4 h, white solid was obtained by filtration (6.45 g, yield: 88.4%).

Workup

  1. temperatureheated to reflux
  2. customthe mixture was reacted for 4 h
  3. customwhite solid was obtained by filtration (6.45 g, yield: 88.4%)

Sources & evidence

ORD record
ord-ba132c04796e4d86846f31313ff0b313
Source dataset
uspto-grants-2015_07
Patent number
US09079892B2

Reaction notes

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