Methyl iodide → Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

HRID 1052228Notes

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

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-c772f0111cc14430aac366327db83f57
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388195B2

Reaction notes

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