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

HRID 1054145

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].[C:33](=O)([O-])[O-:34].[K+].[K+]>O1CCCC1>[O:34]=[C:33]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]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

In a four neck round bottom flask, charged dichloromethane (150 ml), 2-((2R)-2-Hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (15 g), N,N′-dicarbonyldiimidazole (9.22 g), and powdered potassium carbonate (5.24 g) at 25 to 30° C. The obtained reaction mass then stirred for 5 h at 25 to 30° C. Reaction mass then filtered and obtained solid is washed the by dichloromethane. Separated filtrate is concentrated under reduced pressure to obtain residue. Added tetrahydrofuran (30 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. Yield 90%

Workup

customThe obtained reaction mass
customReaction mass
filtrationthen filtered
customobtained solid
washis washed the by dichloromethane
concentrationSeparated filtrate is concentrated under reduced pressure
customto obtain residue
temperatureThe obtained mixture is heated to 40 to 45° C. for 30 minutes
temperatureby cooling to room temperature
filtrationFinally obtained solid is filtered off
washwashed by tetrahydrofuran

Sources & evidence

ORD record: ord-349665e20418469dac7bd7db0eb178df
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394292B2

Linked notes

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