Methyl iodide → Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

HRID 2355281Notes

Reaction equation

HRID 2355281 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=1.[H-].[Na+].[CH3:22]I>CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH3:22])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22710582Methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate

Product 1

HCID 59700597Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoateYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 3-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (2.80 g, 10.6 mmol) in dimethylformamide (60 mL). Add 60% sodium hydride dispersion in oil (0.52 g, 13 mmol). Stir for 1 hr. Add methyl iodide (0.81 mL, 13 mmol) and stir for additional 1 hr. Quench the reaction with water and concentrate. Partition the residue between ethyl acetate and water. Separate the organic layer and dry over sodium sulfate. Filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 15-25% ethyl acetate/hexane to provide the title compound (1.70 g, 57%).

Workup

  1. customQuench
  2. customthe reaction with water
  3. concentrationconcentrate
  4. customPartition the residue between ethyl acetate and water
  5. customSeparate the organic layer
  6. dry with materialdry over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate
  9. customPurify the residue by chromatography (silica gel)
  10. washeluting with 15-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-eff4963b95e2493eae927e542c662d92
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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