Triethylamine → 6-[3-(4-Chlorophenoxyacetylamino)-phenyl]-6-(3-pyridyl)-hex-5-enoic acid

HRID 1975390Notes

Reaction equation

HRID 1975390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH:5]=[CH:6][CH:7]=1.[Cl:23][C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][C:30](Cl)=[O:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:23][C:24]1[CH:34]=[CH:33][C:27]([O:28][CH2:29][C:30]([NH:1][C:2]2[CH:3]=[C:4]([C:8]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][CH:7]=2)=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 53766536Methyl 6-(3-aminophenyl)-6-(3-pyridyl)hex-5-enoate

Product 1

HCID 544068796-[3-(4-Chlorophenoxyacetylamino)-phenyl]-6-(3-pyridyl)-hex-5-enoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.25 g of methyl 6-(3-aminophenyl)-6-(3-pyridyl)-hex-5-enoate are dissolved in 30 ml of methylene chloride. At 0° C., 1.65 g of 4-chlorophenoxyacetic acid chloride and 2.5 ml of triethylamine are added successively to this solution which is then stirred for 2 hours at ambient temperature. The reaction mixture is washed with water and then evaporated down. The residue is dissolved in a mixture of 20 ml of ethanol and 16 ml of 0.5N sodium hydroxide solution and stirred for 24 hours at ambient temperature. The reaction mixture is evaporated down at ambient temperature, water is added and the resulting mixture is washed with ethyl acetate. The aqueous phase is neutralised by the addition of citric acid and extracted with ethyl acetate. The organic phase is washed with water, dried and evaporated down and the residue is recrystallised from ethyl acetate/diisopropyl ether.

Workup

  1. washThe reaction mixture is washed with water
  2. customevaporated down
  3. dissolutionThe residue is dissolved in a mixture of 20 ml of ethanol and 16 ml of 0.5N sodium hydroxide solution
  4. stirringstirred for 24 hours at ambient temperature
  5. customThe reaction mixture is evaporated down at ambient temperature
  6. additionwater is added
  7. washthe resulting mixture is washed with ethyl acetate
  8. additionThe aqueous phase is neutralised by the addition of citric acid
  9. extractionextracted with ethyl acetate
  10. washThe organic phase is washed with water
  11. customdried
  12. customevaporated down
  13. customthe residue is recrystallised from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-f2ebfb8261674e878345efb519bc665f
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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