Sodium Bicarbonate → HCID 69629173, Verbindung

HRID 987330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987330
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[F:31][C:32]([F:44])([F:43])[S:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1.CO.ClCCl>O1CCCC1>[CH2:24]([O:23][C@@H:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][C:41]([NH:40][C:37]3[CH:38]=[CH:39][C:34]([S:33][C:32]([F:43])([F:31])[F:44])=[CH:35][CH:36]=3)=[O:42])=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])[CH3:25]

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 21226129Dichloromethane methanolHCID 86595065HCID 86595065, Verbindung

Produkt 1

HCID 69629173HCID 69629173, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (described in Example 56a) (0.2 g; (0.547 mmole) was dissolved in tetrahydrofuran (5 ml). Sodium hydrogencarbonate (0.051 g; 0.607 mmole) was added and the mixture was stirred for a little while. 4-(Trifluoromethylthio)phenyl isocyanate (0.126 g; 0.575 mmole) was added. The reaction mixture was stirred at room temperature for 6 hours and then evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography of residue on silica gel (isolute, SI) using dichloromethane, methanol:dichloromethane (1:99) and then methanol:dichloromethane (2:98) as eluants gave 0.17 g (57% yield) of (S)-2-ethoxy-3-[4-(2-{4-[({4-[(trifluoromethyl)sulfanyl]anilino}carbonyl)amino]phenyl}ethoxy)phenyl]propanoic acid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 6 hours
  2. customevaporated to dryness
  3. additionEthyl acetate and water were added to the residue
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e3ee2f4384b94cd4ab8f38750f0d97a0
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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