Acetophenone → t-Butyl (2-{4-[3-(4-morpholin-4-yl-phenyl)-3-oxo-propenyl]-benzoylamino}-phenyl)-carbamate

HRID 1180812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180812
[CH:1]([C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:8])=[CH:5][CH:4]=1)=O.[O:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38](=[O:40])[CH3:39])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C(C1C=CC=CC=1)(=O)C.[OH-].[Na+]>CO>[N:29]1([C:32]2[CH:33]=[CH:34][C:35]([C:38](=[O:40])[CH:39]=[CH:1][C:3]3[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:8])=[CH:24][CH:25]=3)=[CH:36][CH:37]=2)[CH2:28][CH2:27][O:26][CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 383624-MorpholinoacetophenoneHCID 22668143Tert-butyl {2-[(4-formylbenzoyl)amino]phenyl}carbamate

Produkt 1

HCID 86602775t-Butyl (2-{4-[3-(4-morpholin-4-yl-phenyl)-3-oxo-propenyl]-benzoylamino}-phenyl)-carbamateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution at room temperature of XI (210 mg, 0.62 mmol), 4′-morpholino acetophenone (227 mg, 1.11 mmol) or acetophenone derivative (1.5–2.0 equiv.) in MeOH (10 ml) was added a solution of NaOH (1.9 ml, 1N in H2O). A precipitate appeared. After 3 days, the reaction mixture was filtered off, rinsed with MeOH, air-dried and dried under vacuum to afford the title compound XXVf (295 mg, 0.56 mmol, 90% yield) as a yellow solid.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered off
  2. washrinsed with MeOH
  3. customair-dried
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b56c569ffb3244489f318879259eb87d
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282608B2

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