Methyl iodide → Methyl N-(tert-butoxycarbonyl)-N-methylglycinate

HRID 1721616Notes

Reaction equation

HRID 1721616 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].[CH3:14]CCCCCC=CCCC.CI>C1C=CC=CC=1>[CH3:14][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

5

Reactant 3

HCID 6328Methyl iodide2×HCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 136496Undec-4-ene

Product 1

HCID 14018930Methyl N-(tert-butoxycarbonyl)-N-methylglycinateYield 86.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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 added 74.94 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, a saturated sodium bicarbonate solution, and then 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

  1. temperatureto reflux for 7 hours
  2. temperaturethe reaction mixture was refluxed
  3. stirringstirred overnight
  4. filtrationThe reaction mixture was filtered
  5. washthe residue washed with ether
  6. washthe combined filtrate was washed with water
  7. dry with materialThe resulting organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-920aef5cd9684cc6be9ea361b41d332f
Source dataset
uspto-grants-1996_04
Patent number
US05512576

Reaction notes

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