Benzenesulfonyl chloride → 2-{benzenesulfonyl-[2-(3-bromo-phenyl)-2-hydroxy-ethyl]-amino}-N-phenyl-acetamide

HRID 560117

반응식

HRID 560117 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:21])[CH2:9][NH:10][CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.OS([O-])(=O)=O.[K+]>C(Cl)Cl>[C:31]1([S:37]([N:10]([CH2:9][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[OH:21])[CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:13])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

6

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 670006572-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide

생성물 1

HCID 670010902-{benzenesulfonyl-[2-(3-bromo-phenyl)-2-hydroxy-ethyl]-amino}-N-phenyl-acetamide수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a cooled suspension of 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide (840 mg) and N,N-diisopropylethylamine (760 mL) in methylene chloride (20 mL) was added benzenesulfonyl chloride (0.31 mL). The mixture was stirred at 0° C. for 1 hour and at room temperature overnight. A 1M aqueous solution of KHSO4 was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, n-heptanelethyl acetate 1:1) to yield 2-{benzenesulfonyl-[2-(3-bromo-phenyl)-2-hydroxy-ethyl]-amino}-N-phenyl-acetamide (1.17 g, 99%) as a white foam, MS: 489.0 (M+H, 1Br)+.

후처리

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, n-heptanelethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-a8fa243c783a4b308a853d399fde4904
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063088B2

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