Sodium hydride → HCID 69601148, 화합물

HRID 2215087노트

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HRID 2215087 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 69601148HCID 69601148, 화합물수율 87.4%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-04ac3bf1e7824e2485fed40bea4996a1
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109223B2

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