Hydrochloric Acid → (S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid

HRID 1377988Notes

Reaction equation

HRID 1377988 reaction equation
[Cl: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][C:3]=1[F:24].C(O)C.[OH-].[Na+].Cl>O>[Cl: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][C:3]=1[F:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 54090463ethyl (S)-8-chloro-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 22821781(S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

57.3 g (164 mmol) of ethyl (S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylate, 40 ml of ethanol, 60 ml of water and 51.5 ml (206 mmol) of 4N sodium hydroxide solution were heated to reflux on a steam bath for 30 min. The alcohol was evaporated on a rotary evaporator. The aqueous phase remaining behind was washed twice with methylene chloride and acidified to pH 3-4 with 51.5 ml (206 mmol) of 4N hydrochloric acid. The suspension obtained was cooled and filtered, and the filter residue was washed with a small amount of ice-water and dried. There were obtained 47.92 g (91%) of (S)-8-chloro-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. 225°-226°.

Workup

  1. temperatureto reflux on a steam bath for 30 min
  2. customThe alcohol was evaporated on a rotary evaporator
  3. washThe aqueous phase remaining behind 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-050df39375aa439085c33495082d7a1f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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