Benzoyl chloride → HCID 53246613, 화합물

HRID 1189581

반응식

HRID 1189581 반응식
[CH3:1][C:2]1[N:3]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:4]([CH3:22])=[CH:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].[Cl-].[Cl-].C([Al+2])C.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[C:34]([C:5]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:15])=[O:16])=[C:2]([CH3:1])[N:3]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:4]=1[CH3:22])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

7

반응물 4

HCID 7412Benzoyl chloride2회HCID 11237Ethylaluminum dichlorideHCID 16686341Ethyl aluminium dichlorideHCID 58310930HCID 58310930, 화합물

생성물 1

HCID 53246613HCID 53246613, 화합물수율 91.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

In a small vial charged with ethyl 2-(2,5-dimethyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (143.7 mg, 0.355 mmol) in DCM (4 mL), at 0° C., was added dropwise a solution of ethylaluminum dichloride (444 μL, 0.444 mmol) in toluene. The reaction mixture turned deep rose color and benzoyl chloride (61.9 μL, 0.533 mmol) was added. The resulting mixture became orange and slowly was allowed to warm to rt. The reaction was stirred 5.25 h and then cooled once again and an additional 800 μL of EtAlCl2 and 150 μL of benzoyl chloride were added. The reaction was once again allowed to warm to room temperature slowly with stirring and stirred an additional 15.25 h at room temperature. The reaction was then quenched by the addition of water and dichloromethane and the water layer was extracted with DCM (3×). The organic layer was dried with MgSO4, and concentrated under vacuum. The crude product was added to a 40 g ISCO silica gel column and purified with a gradient of 0% to 60% EtOAc/hexanes. The product was obtained as a light orange foam (165.2 mg, 0.325 mmol, 91% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 7.92 (dd, 1H), 7.68 (dd, 2H), 7.46 (t, 1H), 7.38-7.32 (m, 3H), 7.20 (t, 1H), 7.10 (d, 1H), 4.56 (s, 2H), 4.30 (s, 2H), 4.24 (q, 2H), 3.23-3.17 (m, 4H), 2.03 (s, 3H), 1.98 (s, 3H), 1.84-1.78 (m, 4H), 1.29 (t, 3H). MS m/z: 509.40 (M+1).

후처리

  1. additionwas added
  2. temperaturecooled once again
  3. temperatureto warm to room temperature slowly
  4. stirringwith stirring
  5. stirringstirred an additional 15.25 h at room temperature
  6. customThe reaction was then quenched by the addition of water and dichloromethane
  7. extractionthe water layer was extracted with DCM (3×)
  8. dry with materialThe organic layer was dried with MgSO4
  9. concentrationconcentrated under vacuum
  10. additionThe crude product was added to a 40 g ISCO silica gel column
  11. custompurified with a gradient of 0% to 60% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-9359d4907be14199a04f8db13c62be8f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674115B2

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