a-(acetyloxy)-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide → (+/-)alpha-Hydroxy-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

HRID 1456150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456150
C([O:4][CH:5]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[CH:28]=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=[O:7])(=O)C>[OH-].[Na+].CO.O>[OH:4][CH:5]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[CH:28]=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=[O:7]

Komponenten

5

Edukt 1

HCID 21837106a-(acetyloxy)-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Produkt 1

HCID 21837018(+/-)alpha-Hydroxy-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 0.34 g of α-(acetyloxy)-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide in 2 ml of 1N NaOH and 4 ml of methyl alcohol is stirred at room temperature for 30 minutes, diluted with 2 ml of water and evaporated in vacuo. The aqueous suspension is extracted with 30 ml of ethyl acetate and the extract washed with brine, dried with Na2SO4 and filtered through a pad of hydrous magnesium silicate and evaporated in vacuo to a residue. The residue is stirred with ether-hexanes to give 0.26 g of cream colored solid. MS(CI): 438(M+H).

Aufarbeitung

  1. customevaporated in vacuo
  2. extractionThe aqueous suspension is extracted with 30 ml of ethyl acetate
  3. washthe extract washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered through a pad of hydrous magnesium silicate
  6. customevaporated in vacuo to a residue
  7. customto give 0.26 g of cream

Quellen und Nachweise

ORD-Eintrag
ord-b54b79a4bf1d430ca642c207f0ffa3a1
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843944

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