Hydrochloric Acid → (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acid

HRID 1378021Notes

Reaction equation

HRID 1378021 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17]CC)=[O:16])=[C:10]3[C@@H:9]3[CH2:20][CH2:21][N:8]3[C:7](=[O:22])[C:6]=2[CH:23]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([OH:17])=[O:16])=[C:10]3[C@@H:9]3[CH2:20][CH2:21][N:8]3[C:7](=[O:22])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53755131ethyl (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto-[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate

Product 1

HCID 22828763(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40.58 g (128.7 mmol) of ethyl (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto-[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate, 300 ml of ethanol and 32.5 ml (130 mmol) of 4N sodium hydroxide solution were heated to reflux on a steam bath for 1.5 hours. The alcohol was evaporated on a rotary evaporator. The aqueous phase was washed twice with methylene chloride and acidified to pH 3-4 with 32.5 ml (130 mmol) of 4N hydrochloric acid. The suspension obtained was cooled and filtered. The filter residue was washed with a small amount of ice water and dried. There were obtained 36.67 g (99%) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid of m.p. 159°-160°.

Workup

  1. temperatureto reflux on a steam bath for 1.5 hours
  2. customThe alcohol was evaporated on a rotary evaporator
  3. washThe aqueous phase was washed twice with methylene chloride
  4. customThe suspension obtained
  5. temperaturewas cooled
  6. filtrationfiltered
  7. washThe filter residue was washed with a small amount of ice water
  8. customdried

Sources & evidence

ORD record
ord-cacbe54dc480410788994dc4e9189cab
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…