Hydrazine hydrate (1:1) → HCID 9882575, compound

HRID 373501Notes

Reaction equation

HRID 373501 reaction equation
C([O:4][C:5]([C@@H:7]1[CH2:22][C@@:15]2([C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:23])[CH:13]=2)[O:8]1)=O)CC.O.[NH2:25][NH2:26]>C(O)C>[F:23][C:12]1[CH:13]=[C:14]2[C@:15]3([C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]3)[CH2:22][C@@H:7]([C:5]([NH:25][NH2:26])=[O:4])[O:8][C:9]2=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67845493Propyl (2S,4S)-6-fluoro-2',5'-dioxo-2,3-dihydrospiro[1-benzopyran-4,4'-imidazolidine]-2-carboxylate

Product 1

HCID 9882575HCID 9882575, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxylic acid n-propyl ester (30.0 g, 93.1 mmol) in 600 ml of ethanol was added hydrazine hydrate (46.6 g, 0.931 mol). After refluxing the mixture under an argon atmosphere for 2 hours, the reaction mixture was evaporated in vacuo to dryness. To the residue was added 100 ml of saturated aqueous sodium chloride and the aqueous layer was extracted with ethyl acetate (300 ml×5). The combined ethyl acetate layers were washed with water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give 17.3 g (Yield: 63.1%) of crude crystals. The crystals were recrystallized from ethanol to give colorless needles of the desired compound (12.8 g, 46.7%).

Workup

  1. temperatureAfter refluxing the mixture under an argon atmosphere for 2 hours
  2. customthe reaction mixture was evaporated in vacuo to dryness
  3. additionTo the residue was added 100 ml of saturated aqueous sodium chloride
  4. extractionthe aqueous layer was extracted with ethyl acetate (300 ml×5)
  5. washThe combined ethyl acetate layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give 17.3 g (Yield: 63.1%) of crude crystals
  10. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-ff35f17f13ab48e7bf8e75b7fd51621f
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

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