4-Methylmorpholine → 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione
Reaction equation
[OH:1][NH:2][C:3](=[O:9])[CH2:4][CH2:5][C:6](N)=[O:7].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[CH3:29][C:30]1([CH2:35][CH2:36][C:37](O)=[O:38])[O:34][CH2:33][CH2:32][O:31]1>ClCCl>[CH3:29][C:30]1([CH2:35][CH2:36][C:37]([O:1][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:9])=[O:38])[O:34][CH2:33][CH2:32][O:31]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
N-Hydroxysuccinamide (0.80 g, 6.9 mmol) followed by 4-methylmorpholine (0.70 g, 6.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (1.32 g, 6.9 mmol) were added to a 0° C. solution of 3-(2-methyl-1,3-dioxolan-2-yl)propanoic acid (1.00 g, 6.24 mmol) in dichloromethane (12 mL). The solution was allowed to warm to room temperature and was stirred overnight. The reaction mixture was diluted with dichloromethane (10 mL), transferred to a separatory funnel, and washed with water (2×10 mL), saturated aqueous sodium bicarbonate (2×10 mL), and brine (10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1.1 g of 1-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione as a white solid.
Workup
- customtransferred to a separatory funnel
- washwashed with water (2×10 mL), saturated aqueous sodium bicarbonate (2×10 mL), and brine (10 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a6fc1ba2574f41f186e503254711630d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897767B2
Reaction notes
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