Potassium Carbonate → 4-[3-[6-(3-Bromo-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester

HRID 418095노트

반응식

HRID 418095 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:21][C:22](=[O:47])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[C:28]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:20]>CC(C)=O.CN(C=O)C>[CH2:19]([O:21][C:22](=[O:47])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:12][C:4]2[CH:5]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:7]=[C:2]([Br:1])[CH:3]=2)[C:28]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:20]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 578630913-Bromo-5-(methylsulfonyl)phenol

생성물 1

HCID 578630554-[3-[6-(3-Bromo-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester수율 87.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a solution of 3-bromo-5-methanesulfonyl-phenol (1.3 g) in a mixture of acetone and DMF (2:1, 60 mL) were added potassium carbonate (7.1 g) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.7 g). The resulting mixture was stirred at 75° C. for 1 day. Then the insoluble material was filtered out and the filtrate was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (2.9 g, 87% yield). LRMS calcd for C30H41O8BrS [M+H]+ 641.2, observed 641.1.

후처리

  1. filtrationThen the insoluble material was filtered out
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified on a silica gel column

출처 및 근거

ORD 기록
ord-993cd84a67d64ce18d998d1371e5e46f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093253B2

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