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

HRID 898646
Notes
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Reaction equation

HRID 898646 reaction equation
[OH:1][C@H:2]([CH2:15][NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C:24]2=[O:29])=[CH:19][CH:18]=1)[CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].[CH2:30]([OH:32])C>C1(C)C=CC=CC=1>[O:32]=[C:30]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[CH:19][CH:18]=2)[CH2:15][C@H:2]([CH2:3][N:4]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:14])[O:1]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 702EthanolHCID 115167582-((2R)-2-hydroxy-3-((4-(3-oxomorpholin-4-yl)phenyl)amino)propyl)-1H-isoindole-1,3(2H)-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
27.5 °C

Procedure

2641 g of 2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (V) are suspended in 22 l of toluene and, at 19° C., 1300 g of N,N-carbonyl-diimidazole are added. The reaction mixture is subsequently heated under reflux for one hour and then, at 60° C., 4.5 l of ethanol are added. After cooling to 25 to 30° C., the precipitated reaction product is filtered off with suction, washed with ethanol and then dried.

Workup

  1. temperatureThe reaction mixture is subsequently heated
  2. temperatureunder reflux for one hour
  3. customthe precipitated reaction product
  4. filtrationis filtered off with suction
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-35367d01c9b445779004fab55b4e50cf
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351823B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes