Dichloromethane → 2-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione
Reaction equation
ClCCl.[OH:4][C@H:5]([CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][C:27]2=[O:32])=[CH:22][CH:21]=1)[CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[O:33]1CCC[CH2:34]1>>[O:33]=[C:34]1[N:19]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C:27]3=[O:32])=[CH:22][CH:21]=2)[CH2:18][C@H:5]([CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[O:4]1Participants
4
Conditions
- Temperature
- 42.5 °C
Procedure
In a four neck round bottom flask, charged dichloromethane (3400 ml), 2-((2R)-2-Hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (340 g) and N,N′-dicarbonyldiimidazole (209.13 g) at 25 to 30° C. The obtained reaction mass then stirred for 8 hr. at 25 to 30° C. Reaction mass is concentrated under reduced pressure to obtain residue. Added tetrahydrofuran (1700 ml) to residue. The obtained mixture is heated to 40 to 45° C. for 30 minutes followed by cooling to room temperature. Finally obtained solid is filtered off and washed by tetrahydrofuran(170 ml)
Workup
- customThe obtained reaction mass
- customat 25 to 30° C
- customReaction mass
- concentrationis concentrated under reduced pressure
- customto obtain residue
- temperatureby cooling to room temperature
- filtrationFinally obtained solid is filtered off
- washwashed by tetrahydrofuran(170 ml)
Sources & evidence
- ORD record
- ord-a4f194c56b274d49952a2fbdbc09f3b0
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394292B2
Reaction notes
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