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 913060ノート

反応式

HRID 913060 の反応式
[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]

参加物

3

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-2dfbe3388f284d0faf1cae0f2e8ef480
出典データセット
uspto-grants-2011_09
特許番号
US08026265B2

反応ノート

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