Sodium hydride → HCID 69601148, compound

HRID 2215087Notes

Reaction equation

HRID 2215087 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@H:9]1[CH2:13][S:12][C:11](=[O:14])[NH:10]1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25].[Cl-].[NH4+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:14]=[C:11]1[N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])[C@@H:9]([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:13][S:12]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 88737Heptanenitrile, 7-bromo-HCID 69601101HCID 69601101, compound

Product 1

HCID 69601148HCID 69601148, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-4 (0.73 g, 3.4 mmol) in 10 mL DMF was added 60% sodium hydride (140 mg, 3.5 mmol) and the resulting solution was stirred for 1 hour at 50° C. whereupon 7-bromoheptanonitrile (1.1 mL, 6.8 mmol) and tetrabutylammonium iodide (50 mg) were added. The solution was stirred at 50° C. overnight afterwhich it was cooled to room temperature, slowly poured into saturated aqueous ammonium chloride solution and was extracted with ether. The organic phases were then combined and sequentially washed with H2O, brine and dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 40–50% ethyl acetate/hexanes to yield 970 mg of 4-1 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 4.63 (m, 1H), 4.04–3.68 (m, 3H), 3.68–3.58 (m, 1H), 3.55 (m, 2H), 3.42 (dd, 1H), 3.22–3.04 (m, 2H), 2.36 (t, 2H), 1.86–1.44 (m, 12H), 1.38–1.30(m, 2H); MS (+ESI): m/z 327.2 (M+1)+.

Workup

  1. additionwere added
  2. temperaturewas cooled to room temperature
  3. extractionwas extracted with ether
  4. washsequentially washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-04ac3bf1e7824e2485fed40bea4996a1
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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