Ammonium Chloride → HCID 178525867, Verbindung

HRID 1620607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620607
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1.C(=O)([O-])O.[Na+].[Cl-].[NH4+]>Cl.C(OCC)(=O)C>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:31]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 178451231HCID 178451231, Verbindung

Produkt 1

HCID 178525867HCID 178525867, VerbindungAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21866389Hydrogen chloride-ethyl acetateLösungsmittel

Versuchsvorschrift

A reaction mixture of tert-butyl N-[(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-2-oxo-2,5-dihydro-1,3-thiazol-4-yl]glycinate (4.8 g) and 4N hydrogen chloride/ethyl acetate (20 mL) was stirred at room temperature for 2 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from methanol/ethyl acetate to give the title compound (3.00 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  6. customrecrystallized from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-30d2119fba5846828a83bad133e4e64d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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