Methyl iodide → Methyl N-(tert-butoxycarbonyl)-N-methylglycinate
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].N12CCCN=C1CCCC[CH2:15]2.CI>C1C=CC=CC=1>[CH3:15][O:12][C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:9]Participants
Procedure
To a solution of N-t-butoxycarbonyl-sarcosine (50 g; 0.264 mol) in 700 ml of benzene was added 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU; 40.19 g, 0.264 mol) in one portion. To the above clear solution was added 74.84 g (0.528 mol) of methyl iodide in one portion and the resulting clear solution was allowed to reflux for 7 hours. After adding additional methyl iodide (16 ml), the reaction mixture was refluxed with stirring and then cooled to room temperature, and stirred overnight. The reaction mixture was filtered, the residue washed with ether, and the combined filtrate was washed with water, saturated sodium bicarbonate solution, and brine. The resulting organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 46.38 g (86.4 %) of N-t-butoxycarbonyl-sarcosine methyl ester as a yellow oil.
Workup
- temperatureto reflux for 7 hours
- temperaturethe reaction mixture was refluxed
- stirringstirred overnight
- filtrationThe reaction mixture was filtered
- washthe residue washed with ether
- washthe combined filtrate was washed with water, saturated sodium bicarbonate solution, and brine
- dry with materialThe resulting organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-dde8614e69a54880bcbec690a016cde2
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556909
Reaction notes
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