Iodoethane → HCID 53664223, compound

HRID 1459403Notes

Reaction equation

HRID 1459403 reaction equation
[C:1]12([NH:11][C:12](=[O:30])[C:13]([CH2:28][OH:29])([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH2:33](I)[CH3:34]>O1CCCC1>[C:1]12([NH:11][C:12](=[O:30])[C:13]([CH2:28][O:29][CH2:33][CH3:34])([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 53924158HCID 53924158, compound

Product 1

HCID 53664223HCID 53664223, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred suspension of N-adamantan-1-yl-2-hydroxymethyl-3-pyridin4-yl-2-pyridin-4-ylmethyl-propionamide (40 mg, 0.1 mmol) in anhydrous tetrahydrofuran (0.50 ml), sodium hydride (7.8 mg of 60% mineral oil dispersion; 0.2 mmol of sodium hydride) was added. After stirring at ambient temperature for 15 minutes, ethyl iodide (15.8 μl, 0.20 mmol) was added. After stirring for 2 hours at ambient temperature, the reaction was quenched by the addition of dilute aqueous sodium bicarbonate/methylene chloride (10 ml of each). The mixture was then extracted with three 10 ml portions of methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate), and concentrated in vacuo to an oil (54 mg). Flash chromatography (silica gel, 40 micron mesh; elution with methanol/ethyl acetate=1:9 in volume) afforded the title compound (free base) (19 mg) as an amorphous solid.

Workup

  1. additionwas added
  2. stirringAfter stirring for 2 hours at ambient temperature
  3. customthe reaction was quenched by the addition of dilute aqueous sodium bicarbonate/methylene chloride (10 ml of each)
  4. extractionThe mixture was then extracted with three 10 ml portions of methylene chloride
  5. dry with materialThe combined organic extracts were dried (anhydrous sodium sulfate)
  6. concentrationconcentrated in vacuo to an oil (54 mg)
  7. washFlash chromatography (silica gel, 40 micron mesh; elution with methanol/ethyl acetate=1:9 in volume)

Sources & evidence

ORD record
ord-4d7dd5e2e3c144d0b54ec211f16e12b7
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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