HCID 14390506, compound → HCID 14390480, compound

HRID 1709586Notes

Reaction equation

HRID 1709586 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[O:17][C:18]([Br:21])=[CH:19][CH:20]=2)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]>C(O)CO.C(O)(C)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:16]1[O:17][C:18]([Br:21])=[CH:19][CH:20]=1)[CH3:2]

Participants

4

Reactant 1

HCID 14390506HCID 14390506, compound

Product 1

HCID 14390480HCID 14390480, compoundYield 1.1%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of N-[3-[(5-bromo-2-furanylcarbonyl)amino]-2-pyridinyl]glycine ethyl ester (110 g, 0.30 mole) was refluxed in ethylene glycol (510 ml) for 2 hours. A 20-ml aliquot (0.01 mole) was removed and water was added to the sample. The product was extracted twice into ethyl acetate and the combined organic layer was washed several times with water, dried over magnesium sulfate, charcoaled, filtered, and evaporated under reduced pressure to give 2.5 g of crude title compound (73% yield). The solid was dissolved in hot isopropyl alcohol, filtered while hot, brought to the cloud point by addition of water and cooled to give a solid which was purified on a column of 20 g of silica gel using 1:1 methylene chloride/ethyl acetate as the eluting solvent. Evaporation of the solvent from the pure fraction gave 1.2 g of product which was recrystallized from isopropyl alcohol/water and dried under high vacuum at room temperature overnight to give 0.88 g of title compound, mp 122.5°-125° C.

Workup

  1. customA 20-ml aliquot (0.01 mole) was removed
  2. additionwater was added to the sample
  3. extractionThe product was extracted twice into ethyl acetate
  4. washthe combined organic layer was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give 2.5 g of crude title compound (73% yield)
  9. filtrationfiltered while hot,
  10. additionbrought to the cloud point by addition of water
  11. temperaturecooled
  12. customto give a solid which
  13. customwas purified on a column of 20 g of silica gel using 1:1 methylene chloride/ethyl acetate as the eluting solvent
  14. customEvaporation of the solvent from the pure fraction

Sources & evidence

ORD record
ord-d55c39406f5e41c7ab6fb460cbd3d97b
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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