Toluene → 2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole

HRID 31607

반응식

HRID 31607 반응식
C1(C)C=CC=CC=1.[CH2:8]1[C:11]2([O:16][CH2:15][CH:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25][C:26]4[NH:30][C:29]5[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=5[N:27]=4)[C:19]=3[CH3:35])[CH2:13][O:12]2)[CH2:10][CH2:9]1.ClC1C=CC=C(C(OO)=[O:44])C=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CO.CO>[CH2:10]1[C:11]2([O:16][CH2:15][CH:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25]([C:26]4[NH:27][C:28]5[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=5[N:30]=4)=[O:44])[C:19]=3[CH3:35])[CH2:13][O:12]2)[CH2:8][CH2:9]1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 597924692-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole

생성물 1

HCID 120031212-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole수율 76.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 21867641Toluene methanol용매

반응 조건

온도
-50 °C

실험 절차

To a toluene (30 ml)/methanol (3 ml) solution of the 2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole (290 mg, 0.73 mmol) obtained in the step (9h), a toluene/methanol (10:1) solution of 3-chloroperbenzoic acid (174 mg, 0.65 mmol as the content was regarded as 65%) was added at −70° C. in a nitrogen atmosphere. After the mixture was stirred at −50° C. for one hour, a saturated aqueous solution of sodium hydrogen carbonate was added. After the mixture was warmed to room temperature, the mixture was extracted with ethyl acetate twice. Organic layers were combined and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1). Fractions containing the title compound was collected by use of ethyl acetate and concentrated. After diethyl ether was added to the residue, the solvent was distilled off to obtain the title compound (230 mg, yield: 76.2%) as a white solid.

후처리

  1. additionwas added at −70° C. in a nitrogen atmosphere
  2. temperatureAfter the mixture was warmed to room temperature
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1)
  8. additionFractions containing the title compound
  9. customwas collected by use of ethyl acetate
  10. concentrationconcentrated
  11. additionAfter diethyl ether was added to the residue
  12. distillationthe solvent was distilled off

출처 및 근거

ORD 기록
ord-9d7d5cdcaaa943238a9ce57c1f8a1516
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

연결된 노트

불러오는 중…