Water → HCID 54031616, compound

HRID 1608553Notes

Reaction equation

HRID 1608553 reaction equation
[CH2:1]([N:4]1[C:12]2[N:11]=[C:10]([C:13]34[CH2:20][CH:19]5[CH2:21][CH:15]([CH2:16][CH:17]3[CH2:18]5)[CH2:14]4)[NH:9][C:8]=2[C:7](=[O:22])[NH:6][C:5]1=[O:23])[CH:2]=[CH2:3].[H-].[Na+].I[CH2:27][CH2:28][CH3:29].O>CN(C)C=O>[CH2:1]([N:4]1[C:12]2[N:11]=[C:10]([C:13]34[CH2:14][CH:15]5[CH2:21][CH:19]([CH2:18][CH:17]3[CH2:16]5)[CH2:20]4)[NH:9][C:8]=2[C:7](=[O:22])[N:6]([CH2:27][CH2:28][CH3:29])[C:5]1=[O:23])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 19097301HCID 19097301, compound

Product 1

HCID 54031616HCID 54031616, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.00 g (3.21 mmol) of Compound G was dissolved in 30 ml of dimethylformamide, and 256 mg of sodium hydride (60%, 6.41 mmol) was added slowly to the solution at 0° C. After 30 minutes, 0.33 ml (3.4 mmol) of 1-iodopropane was added dropwise slowly at the same temperature and stirred at room temperature overnight. The resulting reaction mixture was poured into 300 ml of water, neutralized and extracted three times with 100 ml of chloroform. The organic layer was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: 30% ethyl acetate/hexane) to give 225 mg (yield 20%) of Compound H as a colorless needle crystal.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted three times with 100 ml of chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluate: 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d46e074f59d540e2adb5b37dc32404f0
Source dataset
uspto-grants-1995_03
Patent number
US05395836

Reaction notes

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