1,4-Dioxane → HCID 20038701, compound
Reaction equation
[S:1]1[CH2:5][CH:4]([C:6]([O-])=[O:7])[N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]1.O1CCOCC1.O.[NH3:23]>O1CCCC1>[C:6]([CH:4]1[CH2:5][S:1][CH2:2][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:7])[NH2:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-t-Butyl thiazolidine-3,4-dicarboxylate (2.0 g) was dissolved in tetrahydrofuran (10 ml), and N,N′-carbonyl diimidazole (1.4 g) was added thereto with ice-cooling. The mixture was warmed to room temperature and stirred for 6 hours. 1,4-Dioxane (10 ml) was added thereto, and the mixture was added dropwise to 28% ammonia water (40 ml) cooled on an ice bath. The mixture was warmed to room temperature and stirred for 20 hours. The reaction solution was extracted with ethyl acetate (60 ml). The organic phase was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give t-butyl 4-carbamoylthiazolidine-3-carboxylate (1.6 g, Y.:81%).
Workup
- temperaturewith ice-cooling
- temperaturecooled on an ice bath
- temperatureThe mixture was warmed to room temperature
- stirringstirred for 20 hours
- extractionThe reaction solution was extracted with ethyl acetate (60 ml)
- washThe organic phase was washed with a saturated saline solution
- dry with materialdried over sodium sulfate anhydrous
- concentrationThe product was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f8213438ade54b82b880066a0d1e47dd
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345180B2
Reaction notes
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