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Water → (2-{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

HRID 1161519
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1161519
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[CH3:19][O:20][C:21](=[O:46])[N:22]=[C:23]([S:44][CH3:45])[C:24](=[N:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=1)[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([OH:33])[C:26]=1[F:34].O>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:20][C:21](=[O:46])[N:22]=[C:23]([S:44][CH3:45])[C:24]([C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:26]=1[F:34])=[N:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 72312839[2-(4-Cyanophenylimino)-2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester

Produkt 1

HCID 72312816
(2-{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After adding 0.489 g of cesium carbonate and 0.348 ml of (3-bromopropoxy)-t-butyldimethylsilane to a solution of 0.401 g of [2-(4-cyanophenylimino)-2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester in 10 ml of DMF, the mixture was stirred at room temperature for 24 hours. Next, 50 ml of water was added to the reaction mixture and extraction was performed with 100 ml of ethyl acetate. The organic layer was washed with 50 ml of water and 50 ml of saturated brine in that order and then 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 (ethyl acetate-heptane) to give 0.517 g of the title compound.

Aufarbeitung

  1. washThe organic layer was washed with 50 ml of water and 50 ml of saturated brine in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8cf677cd6cfc4c3e88b7d68e7ffb1e05
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816522B2

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