Methyl iodide → Methyl 4-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

HRID 131277Notes

Reaction equation

HRID 131277 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:22]I>O1CCCC1.C(OCC)(=O)C>[CH3:22][N:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14221817Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoate

Product 1

HCID 17789107Methyl 4-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoateYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[[(tert-butoxycarbonyl)amino]methyl]benzoate (compound obtained in Reference Example 81(1), 2.0 g) in tetrahydrofuran (20 mL) is added sodium hydride (60% dispersion in mineral oil, 0.9 g) under ice-cooling. The mixture is stirred at room temperature for 30 minutes and then to the reaction mixture is added dropwise methyl iodide (2.3 mL). The mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with ethyl acetate, washed with water, and concentrated in vacuo to give methyl 4-[[N-methyl-N-(tert-butoxycarbonyl)amino]-methyl]benzoate (1.9 g, yield; 94%) as a yellow oil. MS (APCI) m/z: 280 [M+H]+

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. washwashed with water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-307dbef7c4144e9681d165ff89ba1cfc
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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