Methyl iodide → HCID 67419815, compound

HRID 1518200Notes

Reaction equation

HRID 1518200 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:29][CH:30]=[CH2:31])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:35]I>CN(C=O)C.C1OCCOCCOCCOCCOC1>[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:29][CH:30]=[CH2:31])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH3:35])=[CH:12][CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67421220HCID 67421220, compound

Product 1

HCID 67419815HCID 67419815, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 3633615-Crown-5Solvent

Procedure

To a solution of allyl-{2-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester (200 mg, 0.44 mmol) in DMF (5 ml), 15-crown-5, and sodium hydride (20 mg, 0.48 mmol) were added, and the mixture was stirred at room temperature for 30 min. Methyliodide (60 mg, 0.44 mmol) was added and the mixture was stirred for 3 h at room temperature. After concentration in vacuo the residue was partitioned between dichloromethane and saturated aqueous NaHCO3. The organic layer was washed with water, dried over MgSO4, filtered and the solvent evaporated under reduced pressure to give the product as a yellow oil (200 mg, 97%).

Workup

  1. stirringthe mixture was stirred for 3 h at room temperature
  2. concentrationAfter concentration in vacuo the residue
  3. customwas partitioned between dichloromethane and saturated aqueous NaHCO3
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-daa57ec8315142299d4843dcbb6078c8
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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