HCID 53999905, compound → HCID 20238644, compound

HRID 364956Notes

Reaction equation

HRID 364956 reaction equation
C(O[CH:4]([O:23]CC)[C:5](=O)[C:6](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[NH2:26][C:27]([CH2:34][F:35])=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(OCC)(=O)C>[F:35][CH2:34][C:27]1[NH:26][C:5]([CH:4]=[O:23])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 53999905HCID 53999905, compoundHCID 73752971HCID 73752971, compound

Product 1

HCID 20238644HCID 20238644, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4,4-diethoxy-2-(3-nitrophenylmethylene)-3-oxobutanoate (21.75 g, 62 mmoles) and ethyl 3-amino-4-fluoro-2-butenoate (9.17 g, 68 mmoles) were heated at 125° for 1.5 hours. The reaction mixture was dissolved in ethyl acetate (150 ml), washed with water and saturated brine, dried (MgSO4) and the solvent was removed in vacuo. The residue was dissolved in tetrahydrofuran (195 ml) and 50% aqueous hydrochloric acid (292 ml) was added slowly. After 30 minutes the reaction mixture was extracted with ethyl acetate and the organic extract washed with saturated aqueous sodium bicarbonate, water, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed on silica eluting with ethyl acetate/petroleum ether (60°-80°) mixtures. Crystallisation from 2-propanol gave the title compound (4.6 g), mp 88°-90°.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in tetrahydrofuran (195 ml)
  5. addition50% aqueous hydrochloric acid (292 ml) was added slowly
  6. extractionAfter 30 minutes the reaction mixture was extracted with ethyl acetate
  7. extractionthe organic extract
  8. washwashed with saturated aqueous sodium bicarbonate, water
  9. dry with materialdried (MgSO4)
  10. customthe solvent was removed in vacuo
  11. customThe residue was chromatographed on silica eluting with ethyl acetate/petroleum ether (60°-80°) mixtures
  12. customCrystallisation from 2-propanol

Sources & evidence

ORD record
ord-d23d12064d8146b4a517293bff4d1d34
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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