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

HRID 1161544ノート

反応式

HRID 1161544 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ee27d4fc2f9343cd8c18974eb1791662
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

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