Dimethylformamide → methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate
Reaction equation
[CH2:1]=[CH:2][CH2:3][CH:4]([OH:6])C.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].Cl.[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][CH2:27][CH3:28])[NH2:24].[CH3:30]N(C=O)C>C(OCC)C>[CH2:4]([O:6][C:7]([NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:8])[CH2:3][CH2:2][CH:1]=[CH2:30]Participants
6
Procedure
To a solution of 1-penten-4-ol (0.95 g, 11.0 mmol) in DMF (15 mL) at 0° C. was added carbonyldiimidazole (1.79 g, 11.0 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min. L-norleucine methyl ester hydrochloride (2.0 g, 11.0 mmol) was then added, the reaction mixture was heated to 50° C. and stirred for 15 min. Upon cooling, the reaction mixture was diluted with ethyl ether and washed twice with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient elution 10 to 90% ethyl acetate in hexanes) to afford 2.1 g (74%) methyl N-[(pent-4-en-1-yloxy)carbonyl]-L-norleucinate as a clear oil.
Workup
- temperaturethe reaction mixture was heated to 50° C.
- stirringstirred for 15 min
- temperatureUpon cooling
- washwashed twice with water
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by silica gel chromatography (gradient elution 10 to 90% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-c3fc7a75ad26475fa2a21056f413a609
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278322B2
Reaction notes
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