Hydrogen chloride-ethyl acetate → HCID 58293287, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9][CH2:8][CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].Cl.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH2:19][NH:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9][CH2:8][CH2:7][NH:6]1)=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(3-benzylaminopropyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.69 g) in chloroform (38 ml) cooled to 0° C. was added 4M hydrochloric acid-ethyl acetate (18 ml), and the mixture was stirred at room temperature for 3 hours. To the mixture was added additional 4M hydrochloric acidethyl acetate (20 ml), and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was concentrated under reduced pressure, and then thereto was added saturated aqueous sodium bicarbonate solution (150 ml). The mixture was extracted with chloroform (100 ml×2, 75 ml×2) 4 times. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (7.49 g).
Workup
- stirringthe mixture was stirred at room temperature for 50 minutes
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionwas added saturated aqueous sodium bicarbonate solution (150 ml)
- extractionThe mixture was extracted with chloroform (100 ml×2, 75 ml×2) 4 times
- dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c3ae9ebecb4048038526484549976952
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609647B2
Reaction notes
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