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

HRID 1161544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161544
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]

Komponenten

7

Edukt 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

Produkt 1

HCID 72312835{2-(4-Cyanophenylimino)-2-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-1-methylsulfanylethylidene}carbamic acid methyl esterAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ee27d4fc2f9343cd8c18974eb1791662
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

Notizen zur Reaktion

Wird geladen…