Methyl iodide → HCID 19735547, compound

HRID 326575Notes

Reaction equation

HRID 326575 reaction equation
[CH2:1]([S:8][C:9]1[NH:10][C:11](=[O:37])[C:12]2[NH:13][CH2:14][N:15]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:40]I>O1CCCC1>[CH2:1]([S:8][C:9]1[N:10]([CH3:40])[C:11](=[O:37])[C:12]2[NH:13][CH2:14][N:15]([C:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 135749800HCID 135749800, compound

Product 1

HCID 19735547HCID 19735547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

After 500 mg (0.10 mmol) of Compound o obtained in Reference Example 14 was dissolved in 20 ml of tetrahydrofuran, 0.08 g (0.20 mmol) of 60% sodium hydroxide was added to the solution under ice cooling. After 30 minutes, 0.125 ml (0.20 mmol) of methyliodide was added, and the mixture was stirred for 2 hours at 50° C. The solvent was evaporated under reduced pressure, and water was added to the residue. The mixture was extracted with chloroform, and the extract was washed with a saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silicagelcolumchromatography (eluent: chloroform) to afford 300 mg (yield, 58%) of Compound p as a white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. washthe extract was washed with a saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silicagelcolumchromatography (eluent: chloroform)
  9. customto afford

Sources & evidence

ORD record
ord-f8ff87a196bc4a76bf01d2a58a5da195
Source dataset
uspto-grants-1993_12
Patent number
US05270316

Reaction notes

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