Methyl iodide → Methyl 5-[(tert-butoxycarbonylamino)methyl]-2-chloro-benzoate

HRID 1469718Notes

Reaction equation

HRID 1469718 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:22]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:19])=[C:14]([CH:18]=1)[C:15]([O:17][CH3:22])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 584833575-(((tert-Butoxycarbonyl)amino)methyl)-2-chlorobenzoic acid

Product 1

HCID 86692228Methyl 5-[(tert-butoxycarbonylamino)methyl]-2-chloro-benzoateYield 41.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-{[(tert-butoxycarbonyl)amino]methyl}-2-chlorobenzoic acid (1.0 g, 3.50 mmol) in DMF (5.0 mL) were added methyl iodide (496 mg, 3.50 mmol) and K2CO3 (966 mg, 7.00 mmol). The reaction mass was stirred at rt for 18 h. The reaction mass was diluted with EtOAc and the organic layer was washed with water and brine. The organic layer was separated, dried, filtered and concentrated. The concentrate was purified by column chromatography to afford 440 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 7.66 (s, 1H), 7.49-7.52 (m, 2H), 7.42 (d, J=6.3 Hz, 1H), 4.13 (d, J=5.7 Hz, 2H), 3.85 (s, 3H), 1.38 (s, 9H).

Workup

  1. washthe organic layer was washed with water and brine
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-ebb8759a32ff44b8be66a10cea2d4e20
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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