Methyl iodide → HCID 15392250, compound

HRID 362534Notes

Reaction equation

HRID 362534 reaction equation
[CH2:1]([O:3][C:4](=[O:43])[CH2:5][S:6](=[O:42])(=[O:41])[N:7]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[CH:23][CH:22]=1)[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([C:19]#[N:20])=[CH:14][CH:15]=2)[CH:10]=1)[CH3:2].CI.[C:46](=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:37]([O:36][C:34]([N:31]1[CH2:32][CH2:33][CH:28]([O:27][C:24]2[CH:23]=[CH:22][C:21]([N:7]([CH2:8][C:9]3[CH:18]=[CH:17][C:16]4[C:11](=[CH:12][C:13]([C:19]#[N:20])=[CH:14][CH:15]=4)[CH:10]=3)[S:6]([CH:5]([CH3:46])[C:4]([O:3][CH2:1][CH3:2])=[O:43])(=[O:41])=[O:42])=[CH:26][CH:25]=2)[CH2:29][CH2:30]1)=[O:35])([CH3:39])([CH3:38])[CH3:40]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11273480HCID 11273480, compound

Product 1

HCID 15392250HCID 15392250, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]acetate (500 mg) was dissolved in 10 ml of acetonitrile, 0.52 ml of methyl iodide and 136 mg of potassium carbonate were added to the solution, and the mixture was stirred under reflux for 5 hours and 30 minutes. After cooling the reaction solution, the precipitate was removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. The resulting residue was applied to silica gel column chromatography, which was eluted with hexane:ethyl acetate (3:1) to give 415 mg of ethyl 2-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]propionate.

Workup

  1. temperatureunder reflux for 5 hours and 30 minutes
  2. temperatureAfter cooling the reaction solution
  3. customthe precipitate was removed by filtration
  4. concentrationthe resulting filtrate was concentrated under a reduced pressure
  5. washwas eluted with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-db29484ce1934f33a90ac24fe27bc3f5
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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