Diisopropylethylamine → 2-(4-fluorophenyl)-2-oxoethyl 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valerate

HRID 2235687노트

반응식

HRID 2235687 반응식
C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[Cl:17][CH2:18][CH2:19][CH2:20]/[C:21](=[CH:25]\[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]2)=[C:28]([O:38][CH3:39])[CH:27]=1)/[C:22]([OH:24])=[O:23].[F:40][C:41]1[CH:50]=[CH:49][C:44]([C:45](=[O:48])[CH2:46]Br)=[CH:43][CH:42]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][CH2:18][CH2:19][CH2:20]/[C:21](=[CH:25]\[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]2)=[C:28]([O:38][CH3:39])[CH:27]=1)/[C:22]([O:24][CH2:46][C:45]([C:44]1[CH:49]=[CH:50][C:41]([F:40])=[CH:42][CH:43]=1)=[O:48])=[O:23]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 86585896Sodium bicarbonate water

생성물 1

HCID 670673172-(4-fluorophenyl)-2-oxoethyl 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valerate수율 40.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

IPEA (0.14 mL) was added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid trifluoroacetic acid salt (110 mg) and 4-fluorophenacyl bromide (85 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for 30 minutes. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 47 mg of the title compound. The property values of the compound are as follows.

후처리

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

출처 및 근거

ORD 기록
ord-af08c59154f34db6afff4cc159da4611
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713993B2

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