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

HRID 1670071노트

반응식

HRID 1670071 반응식
[CH2:1]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12]([OH:17])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:27][C:28](=[O:53])[CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]Br)[C:34]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH3:26]>CC(C)=O.CN(C=O)C>[CH2:25]([O:27][C:28](=[O:53])[CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:17][C:12]2[CH:13]=[C:14]([I:16])[CH:15]=[C:10]([C:9](=[O:18])[NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=2)[C:34]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH3:26]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 57905909N-Benzyl-3-hydroxy-5-iodo-benzamide

생성물 1

HCID 673378574-[3-[6-(3-Benzylcarbamoyl-5-iodo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester수율 100.8%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a solution of N-benzyl-3-hydroxy-5-iodo-benzamide (4.1 g) in a mixture of acetone and DMF (2:1, 100 mL) were added potassium carbonate (16.0 g) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (6.0 g). The resulting mixture was stirred at 75° C. for 2 days. 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 8.7 g of yellow oil (100% yield).

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-e6446ac18dbb4d38b0bd7610bc4d2b65
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989454B2

반응 노트

불러오는 중…