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

HRID 1523702Notes

Reaction equation

HRID 1523702 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+]>C(OCC)(=O)C>[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 83.86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 ethyl acetate (70 mL) respectively, lithium bromide (0.15 g, 1.74 mmol) was added at 20° C., reacted for 12 h. White solid was obtained by filtration (6.11 g, yield: 83.86%).

Workup

  1. customreacted for 12 h
  2. customWhite solid was obtained by filtration (6.11 g, yield: 83.86%)

Sources & evidence

ORD record
ord-4339f13ff0d04db7b19912f8727aacb8
Source dataset
uspto-grants-2015_07
Patent number
US09079892B2

Reaction notes

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