Water → Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate

HRID 1797735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797735
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[N:11]=[CH:12][S:13][CH:14]=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:33]([O:37][C:38](=[O:63])[NH:39][CH2:40][C:41]1[N:42]([CH2:59][CH:60]([CH3:62])[CH3:61])[C:43](=[O:58])[C:44]2[C:49]([C:50]=1[O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:47]([CH:56]=O)=[CH:46][CH:45]=2)([CH3:36])([CH3:35])[CH3:34].O>CN(C)C=O>[C:33]([O:37][C:38](=[O:63])[NH:39][CH2:40][C:41]1[N:42]([CH2:59][CH:60]([CH3:61])[CH3:62])[C:43](=[O:58])[C:44]2[C:49]([C:50]=1[O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:47](/[CH:56]=[CH:9]/[C:10]1[N:11]=[CH:12][S:13][CH:14]=1)=[CH:46][CH:45]=2)([CH3:36])([CH3:34])[CH3:35]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22175328Triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chlorideHCID 22176124Tert-butyl (4-butoxy-6-formyl-2-isobutyl-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate

Produkt 1

HCID 22175662Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamateAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chloride (0.44 g, 1.1 mmol), potassium carbonate (15 g, 1.1 mmol) and tert-butyl(4-butoxy-6-formyl-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.47 g, 1.1 mol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 10 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.46 g, 80.7%) as crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crystals were recrystallized from ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f7e34a5deabb45af8102e008c8013593
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034039B2

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