Acetic Acid → {2-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 1161544노트

반응식

HRID 1161544 반응식
C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:23][O:24][C:25](=[O:60])[N:26]=[C:27]([S:58][CH3:59])[C:28]([C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH2:47][CH2:48][O:49][Si](C(C)(C)C)(C)C)[C:39]=1[F:57])=[N:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:23][O:24][C:25](=[O:60])[N:26]=[C:27]([S:58][CH3:59])[C:28](=[N:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][CH:35]=1)[C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH2:47][CH2:48][OH:49])[C:39]=1[F:57]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 72312754(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

생성물 1

HCID 72312835{2-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-1-methylsulfanylethylidene}carbamic acid methyl ester수율 80.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

After adding 0.09 ml of acetic acid and 1.3 ml of TBAF (1.0 M, THF solution) to a solution of 616 mg of (2-{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester (Example (181a)) in 5 ml of THF, the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (394 mg, isomeric mixture) as a light yellow solid.

후처리

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

출처 및 근거

ORD 기록
ord-ee27d4fc2f9343cd8c18974eb1791662
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

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