Hydrochloric Acid → 4-(4-((5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl)phenyl)morpholin-3-one hydrochloride
Reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[O:3]1.CN.[ClH:34]>CO>[ClH:34].[NH2:21][CH2:20][C@@H:4]1[O:3][C:2](=[O:1])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 27.5 °C
Procedure
In a four neck round bottom flask, charged methanol (100 ml), 2-([(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (10 g), and 40% aqueous methylamine (5 g) at 25 to 30° C. Reaction mass is stirred for 1 h at 25 to 30° C. Added second lot of 40% aqueous methylamine (5 g) to reaction mass at 25 to 30° C. After complete addition of methylamine solution, reaction mass is heated to 60 to 65° C., and maintained at same temperature for 4 h. Reaction mixture then cooled to 25 to 30° C. and added conc. hydrochloric acid (2 ml, pH should be 1 to 2). Finally reaction mass is cooled to 10° C. and stirred for 30 minutes. Obtained solid is filtered off and washed by chilled methanol (10 ml). Yield 80%
Workup
- customReaction mass
- customto reaction mass at 25 to 30° C
- temperatureis heated to 60 to 65° C.
- temperaturemaintained at same temperature for 4 h
- customReaction mixture
- temperaturethen cooled to 25 to 30° C.
- customFinally reaction mass
- temperatureis cooled to 10° C.
- stirringstirred for 30 minutes
- customObtained solid
- filtrationis filtered off
- washwashed
- temperatureby chilled methanol (10 ml)
Sources & evidence
- ORD record
- ord-19ced85e9b3c46a19cd2a27ef51a221c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394292B2
Reaction notes
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