6-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol → 9-Hydroxy-9-[5(2-naphthyl)-1H-imidazol-2-yl]nonan-3-one

HRID 913060노트

반응식

HRID 913060 반응식
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[N:19]=2)[OH:14])OCC[O:4]1)[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:14][CH:13]([C:15]1[NH:19][C:18]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[CH:17][N:16]=1)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3](=[O:4])[CH2:1][CH3:2]

참가 물질

3

반응물 1

HCID 673820876-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol

생성물 1

HCID 673818489-Hydroxy-9-[5(2-naphthyl)-1H-imidazol-2-yl]nonan-3-one

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

The alcohol F2 was dissolved in TFA/DCM (1:1) and stirred for 4 hr at RT. The reaction was quenched with sat. aq. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and solvent was removed under reduced pressure. The crude product was purified by flash chromatography, using EtOAc/petroleum ether as eluents and the product was obtained as a white solid. 1H NMR (300 MHz, DMSO) δ: 8.30 (1H, s), 7.97-7.75 (6H, m), 7.58-7.41 (2H, m), 5.81 (1H, br s), 4.75 (1H, m), 2.37 (4H, m), 1.80 (2H, m), 1.51-1.19 (6H, m), 0.88 (3H, t, J=7.3 Hz). MS (ES) C22H26N2O2 requires: 350, found: 351 (M+H)+.

후처리

  1. customThe reaction was quenched with sat. aq. NaHCO3 solution
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4) and solvent
  4. customwas removed under reduced pressure
  5. customThe crude product was purified by flash chromatography
  6. customthe product was obtained as a white solid

출처 및 근거

ORD 기록
ord-2dfbe3388f284d0faf1cae0f2e8ef480
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026265B2

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