Sodium Hydroxide → HCID 53891595, compound

HRID 1378061Notes

Reaction equation

HRID 1378061 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][CH2:24][N:10]3[C:9](=[O:25])[C:8]=2[C:26]=1[F:27]>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][CH2:24][N:10]3[C:9](=[O:25])[C:8]=2[C:26]=1[F:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53770341HCID 53770341, compound

Product 1

HCID 53891595HCID 53891595, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20.7 ml (82.7 mmol) of 4N sodium hydroxide solution were added dropwise to a suspension of 22.1 g (63.6 mmol) of ethyl (5)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate in 55 ml of ethanol and 90 ml of water and heated at reflux for 45 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 with sodium sulfate, filtration and evaporation yielded 20 g (98%) of (S)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid as colourless crystals of m.p. 214.5°-215.5° (dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 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 with sodium sulfate, filtration and evaporation

Sources & evidence

ORD record
ord-3ab3a414fe9748bfa7a5f0890e0fca8d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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