Ethanol → 5,6,7,8-Tetrahydro-5-oxo-4H-furo[3,2-b]azepine-3-carboxylic acid

HRID 862996Notes

Reaction equation

HRID 862996 reaction equation
CC1C=CC(S(O/[N:12]=[C:13]2\[CH2:14][CH2:15][CH2:16][C:17]3[O:21][CH:20]=[C:19]([C:22]([OH:24])=[O:23])[C:18]\2=3)(=O)=O)=CC=1.C([O-])(=[O:27])C.[K+].C(O)C>O>[O:27]=[C:13]1[NH:12][C:18]2[C:19]([C:22]([OH:24])=[O:23])=[CH:20][O:21][C:17]=2[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 702EthanolHCID 517044Potassium AcetateHCID 19699104HCID 19699104, compound

Product 1

HCID 196991005,6,7,8-Tetrahydro-5-oxo-4H-furo[3,2-b]azepine-3-carboxylic acidYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g of (E)-4,5,6,7-tetrahydro-4-[[[(4-methylphenyl)sulfonyl]oxy]imino]-3-benzofurancarboxylic acid, 5.9 g of potassium acetate, 23 ml of ethanol and 39 ml of water is heated at reflux for 48 hours. The reaction mixture is concentrated in vacuo, 80 ml of methylene chloride added and the separated organic layer washed with water, brine and dried with Na2SO4. The organic layer is concentrated in vacuo to a solid which is purified by chromatography on a preparative silica gel plate by elution with 0.5% acetic acid in ethyl acetate. The eluted band is washed with 1% acetic acid in ethyl acetate. The organic layer is dried with Na2SO4 and concentrated in vacuo to give 200 mg of off-white solid which is crystallized from ethyl acetate-hexane to give 165 mg of the desired product as a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. concentrationThe reaction mixture is concentrated in vacuo, 80 ml of methylene chloride
  4. additionadded
  5. washthe separated organic layer washed with water, brine
  6. dry with materialdried with Na2SO4
  7. concentrationThe organic layer is concentrated in vacuo to a solid which
  8. customis purified by chromatography on a preparative silica gel plate by elution with 0.5% acetic acid in ethyl acetate
  9. washThe eluted band is washed with 1% acetic acid in ethyl acetate
  10. dry with materialThe organic layer is dried with Na2SO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-532e737546ea4dd989b8e39419290ec0
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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