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Hydrochloric Acid → 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979416
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1979416
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([C:14]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[O:15])[CH2:4][CH:3]1[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])=[O:32].[OH-].[Na+].Cl>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:34]1([CH3:39])[C:33]([C:31]([CH2:30][N:8]2[C:7]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=3[N:5]([C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[O:15])[CH2:4][CH:3]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:2]2=[O:1])=[O:32])=[CH:38][CH:37]=[CH:36][CH:35]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124306762-Bromo-2'-methylacetophenoneHCID 212018672-oxo-3-tert-butoxycarbonylamino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212016051-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine
Ausbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Oxo-3-tert-butoxycarbonylamino-5-(furan-2-ylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.50 g) was suspended in toluene (20 ml), 2-bromo-2′-methylacetophenone (995 mg), 1N aqueous sodium hydroxide (10 ml) and tetra n-butylammonium bromide (20 mg) were added, and the mixture was stirred for 2 hours at room temperature. The reaction mixture was weakly acidified with 1N hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:ethyl acetate=20:1), to thereby obtain 1.55 g of the titled compound (Yield: 76.9%).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography(chloroform:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-1fce22a7a2ef4462bcea593c4eed839f
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06239131B1

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