Triethylamine → HCID 23323872, compound

HRID 1381376Notes

Reaction equation

HRID 1381376 reaction equation
[C:1]([O:4][C:5]1[C:9](=[O:10])[O:8][CH:7]([CH2:11][CH2:12]C(O)=O)[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:3])[CH3:2].C([N:24](CC)CC)C.[C:29](Cl)(=[O:33])[O:30][CH2:31]C.[N-]=[N+]=[N-].[Na+]>CC(C)=O.O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:9](=[O:10])[O:8][CH:7]([CH2:11][CH2:12][NH:24][C:29](=[O:33])[O:30][CH3:31])[C:6]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 13893921HCID 13893921, compound

Product 1

HCID 23323872HCID 23323872, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent3×HCID 962WaterSolventHCID 21584013Chloroform ethylacetateSolvent

Procedure

3-(4-Acetoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (58 mg) was dissolved in acetone (2 ml), and a solution of triethylamine (32 μl) in acetone (5 ml) was added with ice-cooling. Then, a solution of ethyl chlorocarbonate (24 μl) in acetone (2 ml) was added dropwise slowly. The mixture was stirred with ice-cooling for 30 minutes, and a solution of sodium azide (19.5 mg) in water (1 ml) was added. The mixture was stirred with ice-cooling for 1 hour, poured into ice water, and extracted with ether. After removal of the ether by distillation, benzene (5 ml) was added, and the mixture was heated under reflux for 1 hour. After cooling, methanol (2 ml) was added, and the mixture was allowed to stand at room temperature overnight. The solvent was distilled off to give 56 mg of a crude product. This was subjected to preparative silica gel thin layer chromatography (0.5 mm×3, Merck) using chloroform-ethyl acetate (5:1 ) as the developing solvent to give methyl N-2-(4-acetoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)ethylcarbamate (43 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringThe mixture was stirred with ice-
  4. temperaturecooling for 1 hour
  5. extractionextracted with ether
  6. customAfter removal of the ether
  7. distillationby distillation, benzene (5 ml)
  8. additionwas added
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 1 hour
  11. temperatureAfter cooling
  12. additionmethanol (2 ml) was added
  13. distillationThe solvent was distilled off
  14. customto give 56 mg of a crude product

Sources & evidence

ORD record
ord-2e6fcac15a0b49de8c895898a995c459
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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