Sodium hydride → HCID 178448628, 화합물

HRID 340648

반응식

HRID 340648 반응식
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1F)[CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])[CH2:11][CH2:12][CH3:13]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 247470IsopentyldiolHCID 178448621HCID 178448621, 화합물

생성물 1

HCID 178448628HCID 178448628, 화합물수율 90.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
2.5 °C

실험 절차

3-Methylbutane-1,3-diol (42 mg, 0.4 mmol) in THF (1 mL) was treated with NaH (60%) (16 mg, 0.4 mmol) at room temperature for 20 min. To the above mixture, which was cooled to 0-5° C., was added the product from Example 20B (80 mg, 0.2 mmol) in THF (1 mL). After 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 87 mg (90%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.04 (t, J=7.32 Hz, 3H) 1.36 (s, 6H) 1.47-1.55 (m, 2H) 1.88-1.96 (m, 2H) 2.13 (t, J=5.80 Hz, 2H) 4.35 (t, J=5.80 Hz, 2H) 4.54 (t, J=7.63 Hz, 2H) 5.12 (brs, 1H) 7.11 (d, J=8.54 Hz, 1H) 7.61 (d, J=5.19 Hz, 1H) 7.74 (dd, J=8.54, 2.14 Hz, 1H) 8.49 (d, J=5.19 Hz, 1H) 8.68 (s, 1H) 8.72 (s, 1H); MS (ESI+) m/z 482 (M+H)+.

후처리

  1. customAfter 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4fbaf80223a743fe9d8a03d24f29aea6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895592B2

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