Methyl iodide → Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]=[CH2:15])[C:10]([O:12][CH3:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (20.0 g), potassium carbonate (13.2 g) and N,N-dimethylformamide (100 mL) was stirred for 15 min. The mixture was cooled to 0° C., iodomethane (9.2 g) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was filtered, and the residue was washed with ethyl acetate. The filtrate was successively washed with 5% hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (21.0 g).
Workup
- stirringthe mixture was stirred at room temperature for 2 hr
- filtrationThe reaction mixture was filtered
- washthe residue was washed with ethyl acetate
- washThe filtrate was successively washed with 5% hydrochloric acid and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationInsoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-67338357997f4b40873b411b8e8c5039
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722660B2
Reaction notes
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