Iodoethane → HCID 178477481, compound

HRID 2227472Notes

Reaction equation

HRID 2227472 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([NH:28][C:29]([NH2:31])=[S:30])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32](I)[CH3:33]>CC(C)=O>[C:12]([O:11][C:9]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([NH:28][C:29](=[NH:31])[S:30][CH2:32][CH3:33])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27]1)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 18474004HCID 18474004, compound

Product 1

HCID 178477481HCID 178477481, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the compound (55 mg) obtained in Example 1f, ethyl iodide (0.039 ml) and acetone (5 ml) was heated under reflux for 14 hours and then concentrated at reduced pressure. Saturated sodium hydrogencarbonate solution was added to the resulting residue and extraction with ethyl acetate was conducted. The organic layer was washed with brine, dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=4:6) to give the titled compound (yield, 77%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 14 hours
  3. concentrationconcentrated at reduced pressure
  4. additionSaturated sodium hydrogencarbonate solution was added to the resulting residue and extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=4:6)

Sources & evidence

ORD record
ord-9b5adccb807a4674a698a84939161107
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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