Trifluoroacetic acid → HCID 178449064、化合物

HRID 528996ノート

反応式

HRID 528996 の反応式
[CH2:1]([N:5]([CH2:43][CH2:44][CH2:45][CH3:46])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[N:11](COCC[Si](C)(C)C)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:43]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[NH:11][CH:12]=1)=[O:7])[CH2:44][CH2:45][CH3:46]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 71062252Methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

生成物 1

HCID 178449064HCID 178449064、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (180 mg, 0.28 mmol) in DCM (4 mL) was added trifluoroacetic acid (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 4 h. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in DCM and washed with sat. NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated to give crude product. The crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3) to provide the title compound (130 mg, 91%). 1H NMR (CD3OD) δ 8.25-8.06 (m, 2H), 8.00-7.50 (m, 2H), 7.28-6.83 (m, 4H), 4.36 (br s, 1H), 4.01 (br s, 4H), 3.60-3.24 (m, 6H), 2.88-2.69 (m, 2H), 1.60-1.52 (m, 4H), 1.36-1.30 (m, 4H), 1.05-0.90 (m, 6H); MS(ESI−) m/z 515.2 (M−H)−.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in DCM
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3)

出典と根拠

ORDレコード
ord-e2460e09de5942c790bc1da60c1f4e89
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

反応ノート

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