tert-Butanol → HCID 67360378, 화합물

HRID 1747475노트

반응식

HRID 1747475 반응식
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH:18]=[CH:19][NH:20]3)[C:7]1=[O:26].C([OH:32])(C)(C)C>[Zn]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH2:18][C:19](=[O:32])[NH:20]3)[C:7]1=[O:26]

참가 물질

4

반응물 2

HCID 6386tert-ButanolHCID 67361638HCID 67361638, 화합물

생성물 1

HCID 67360378HCID 67360378, 화합물수율 36%

시약·촉매·용매 1

HCID 23994Zinc촉매

실험 절차

3-[3-(6-Chloro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (248 mg, 0.64 mmol) is dissolved it tert-butanol (20 mL) at 40° C. The reaction is stirred and pyridiniumtrbromide is added portion wise over 5 minutes. The reaction is stirred for 10 minutes and concentrated in vacuo. The crude material is dissolved in acetic acid (10 mL) and zinc powder (211 mg, 3.2 mmol)is added to the reaction. The reaction is stirred at room temperature for one hour, then the solvent evaporated in vacuo. The residue is taken up in dimethyl sulfoxide and filtered. The crude material is purified by preparative reverse phase LC to give the title compound (34 mg 0.09 mmol, 36%).

후처리

  1. additionpyridiniumtrbromide is added portion wise over 5 minutes
  2. stirringThe reaction is stirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material is dissolved in acetic acid (10 mL)
  5. stirringThe reaction is stirred at room temperature for one hour
  6. customthe solvent evaporated in vacuo
  7. filtrationfiltered
  8. customThe crude material is purified by preparative reverse phase LC

출처 및 근거

ORD 기록
ord-2874c84eeabf4447a908dee6f6c191d3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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