Potassium Cyanide → isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 67328

Reaktionsgleichung

Reaktionsgleichung von HRID 67328
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.[C-:24]#N.[K+]>CC(O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH:19]([CH3:24])[CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12

Komponenten

4

Edukt 2

HCID 9032Potassium Cyanide2×HCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

Produkt 1

HCID 54047224isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

934 mg (3 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate are stirred at 60° C. for 48 hours with 198 mg (3 mmol) of potassium cyanide in 30 ml of dry 2-propanol. The mixture is evaporated in vacuo. The residue is treated with 30 ml of 2-propanol and 198 mg (3 mmol) of potassium cyanide and heated to boiling under reflux for 22 hours. After evaporation in vacuo, the residue is treated with water and extracted three times with 30 ml of chloroform each time. The combined chloroform phases are washed three times with 20 ml of water each time, dried over magnesium sulphate and evaporated. After recrystallisation from ethyl acetate/n-hexane, there is obtained isopropyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 207°-208° C.

Aufarbeitung

  1. customThe mixture is evaporated in vacuo
  2. temperatureheated
  3. temperatureunder reflux for 22 hours
  4. customAfter evaporation in vacuo
  5. additionthe residue is treated with water
  6. extractionextracted three times with 30 ml of chloroform each time
  7. washThe combined chloroform phases are washed three times with 20 ml of water each time
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customAfter recrystallisation from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ab602c976b4e4ba7b37ddb85c0d566f3
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346030

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