Hydrochloric Acid → (S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one
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.Cl>C(O)C>[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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 61.5 °C
Procedure
1360 g of 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (VI) are suspended in 10.2 l of ethanol at 22° C., and 1103 g of methylamine solution (40% strength in water) are added. The reaction mixture is then heated to 60 to 63° C., and the resulting solution is stirred at this temperature for 2 hours. After cooling to 55 to 60° C., a total of 2348 g of hydrochloric acid solution (20% strength in water) is added until the pH is 2.7, after which the product starts to crystallize. After cooling to 20° C., the precipitated reaction product is filtered off with suction, washed with methanol and then dried.
Workup
- temperatureAfter cooling to 55 to 60° C.
- customto crystallize
- temperatureAfter cooling to 20° C.
- customthe precipitated reaction product
- filtrationis filtered off with suction
- washwashed with methanol
- customdried
Sources & evidence
- ORD record
- ord-15edc5b795db46788c2291aa0efded7e
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351823B2
Reaction notes
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