Hydrochloric Acid → HCID 86724967, compound
Reaction equation
COC[O:4][CH2:5][C@@H:6]1[CH2:10][N:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH2:18][C:17](=[O:20])[NH:16][C:15]=3[CH:21]=2)[C:8](=[O:22])[CH2:7]1.O1CCCC1.Cl.ClCCl>CO>[OH:4][CH2:5][C@@H:6]1[CH2:10][N:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH2:18][C:17](=[O:20])[NH:16][C:15]=3[CH:21]=2)[C:8](=[O:22])[CH2:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 6-{(4S)-4-[(methoxymethoxy)methyl]-2-oxopyrrolidin-1-yl}-2H-1,4-benzoxazin-3(4H)-one (1.49 g, 4.86 mmol) in methanol (10 ml)/tetrahydrofuran (10 ml) was added 4N Hydrochloric acid (2 ml) at room temperature and the mixture was heated to 60° C. and stirred for 18 hours. The reaction solution was poured into a mixture of dichloromethane and a saturated sodium hydrogen carbonate aqueous solution and the resultant was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. A mixed solvent of dichloromethane/methanol (10:1) was added to the obtained solid to prepare a slurry and the solid was collected by filtration to yield 1.14 g (90%) of the title compound in the form of a light yellow solid.
Workup
- extractiona saturated sodium hydrogen carbonate aqueous solution and the resultant was extracted with dichloromethane
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe drying agent was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- additionA mixed solvent of dichloromethane/methanol (10:1) was added to the obtained solid
- customto prepare a slurry
- filtrationthe solid was collected by filtration
Sources & evidence
- ORD record
- ord-ed094809f8a94e87aa5c895338655770
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952010B2
Reaction notes
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