Hydroxylamine → (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime

HRID 867531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867531
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:22][OH:23]>C(O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:22][OH:23])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 54287641(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

Produkt 1

HCID 53703069(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

7.0 g (23.4 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile are stirred at boiling temperature for 1.5 hours together with about 1.0 g of freshly prepared hydroxylamine in 90 ml of ethanol. By cooling, filtering off the precipitated material, washing with ether and drying there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime of melting point 249°-250°. By chromatography of the residue from the mother liquor on silica gel and subsequent crystallization from ethyl acetate there is obtained a second portion of the desired amidoxime.

Aufarbeitung

  1. customfor 1.5 hours
  2. temperatureBy cooling
  3. filtrationfiltering off the precipitated material
  4. washwashing with ether
  5. customdrying there

Quellen und Nachweise

ORD-Eintrag
ord-e36f1d1892084c639e94e7c85e3c8488
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775671

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