Methyl iodide → HCID 68817735, compound

HRID 736836Notes

Reaction equation

HRID 736836 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:37](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:37][N:23]([S:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)=[CH:19][CH:18]=1)(=[O:22])=[O:21])[C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68818235HCID 68818235, compound

Product 1

HCID 68817735HCID 68817735, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of 125 mg of tert-butyl trans-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylate in 4 mL of N,N-dimethylformamide was added 133 mg of potassium carbonate, followed by 68 mg of iodomethane. The suspension was stirred at room temperature over night. After removal of the volatile material in vacuo, 80 ml of ethyl acetate was added. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was to provide 121 mg (97% yield) of tert-butyl trans-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylate after flash column chromatography eluting with ethyl acetate/hexane (3:7). MS: 525.2 (M+H)+

Workup

  1. customAfter removal of the volatile material in vacuo, 80 ml of ethyl acetate
  2. additionwas added
  3. washThe organic phase was washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4576abd6e72b482093af7dc0f0aedc39
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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