Hydrochloric Acid → (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid

HRID 1378163Notes

Reaction equation

HRID 1378163 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]3[CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18]CC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C.Cl>O>[Br:1][C:2]1[C:7]2[C:8](=[O:23])[N:9]3[CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([OH:18])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 53712300ethyl (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto [2,1-c]imidazo [1,5-a][1,4]benzodiazepine-1-carboxylate

Product 1

HCID 22876624(S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21.8 g (57.9 mmol) of ethyl (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto [2,1-c]imidazo [1,5-a][1,4]benzodiazepine-1-carboxylate were heated to reflux for 15 minutes with 17 ml of 4N sodium hydroxide solution and 200 ml of ethanol. 17 ml of 4N hydrochloric acid and 250 ml of water were added at room temperature. The alcohol was evaporated and the suspension was cooled to 0°. By suction filtration and drying the crystals there were obtained 19.8 g (98%) of (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acid of m.p. 178°-180°.

Workup

  1. customThe alcohol was evaporated
  2. temperaturethe suspension was cooled to 0°
  3. filtrationBy suction filtration
  4. customdrying the crystals

Sources & evidence

ORD record
ord-879239a3f2784c7c88be4c9eca986a79
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…