Sodium Hydroxide → HCID 54483365, compound

HRID 1378010Notes

Reaction equation

HRID 1378010 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([O:19]CC)=[O:18])=[C:12]3[C@@H:11]3[CH2:22][CH2:23][N:10]3[C:9](=[O:24])[C:8]=2[C:25]=1[F:26]>C(O)C.O>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([OH:19])=[O:18])=[C:12]3[C@@H:11]3[CH2:22][CH2:23][N:10]3[C:9](=[O:24])[C:8]=2[C:25]=1[F:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53890045HCID 53890045, compound

Product 1

HCID 54483365HCID 54483365, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8.6 ml (34.3 mmol) of 4N sodium hydroxide solution were added dropwise to a suspension of 8.8 g (26.4 mmol) of ethyl (S)-7,8-difluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate in 20 ml of ethanol and 30 ml of water and the mixture was heated at reflux for 30 minutes. Subsequently, the ethanol was distilled off. The aqueous phase was washed twice with methylene chloride and adjusted to pH=3 with 4N hydrochloric acid. Extraction with methylene chloride (five times), drying over sodium sulfate, filtration and evaporation yielded 7.2 g (89%) of (S)-7,8-difluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid as colourless needles of m.p. 218.0°-219.5° (dec.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. distillationSubsequently, the ethanol was distilled off
  4. washThe aqueous phase was washed twice with methylene chloride
  5. extractionExtraction with methylene chloride (five times)
  6. dry with materialdrying over sodium sulfate, filtration and evaporation

Sources & evidence

ORD record
ord-229e6b73dc814939ba66e92a7493f37b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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