Triethylamine → 5-(4'-Ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamide

HRID 654340Notes

Reaction equation

HRID 654340 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:4][C:3]=1[O:15][CH3:16].C(N(CC)CC)C.[C:24](Cl)(=[O:28])[O:25][CH2:26][CH3:27].[CH2:30]([NH2:35])[CH:31]=[C:32]([CH3:34])[CH3:33]>C(Cl)Cl>[CH2:30]([NH:35][C:12](=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][C:24]([O:25][CH2:26][CH3:27])=[O:28])=[C:3]([O:15][CH3:16])[CH:4]=1)[CH:31]=[C:32]([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1669212-Buten-1-amine, 3-methyl-HCID 542168095-(4-Hydroxy-3-methoxyphenyl)penta-2,4-dienoic acid

Product 1

HCID 543244305-(4'-Ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

In 50 ml of methylene chloride is suspended 2.20 g of 5-(4'-hydroxy 3'-methoxyphenyl)pentadienoic acid under an argon atmosphere. To the suspension cooled to -10° C. are added 2.92 ml of triethylamine and 2.16 g of ethyl chlorocarbonate. To the mixture, after stirred for one hour, is added a solution of 1.28 g of prenylamine in 10 ml of methylene chloride, and the resulting mixture is stirred at -10° C. to 0° C. for 3 hours. The reaction mixture is poured onto water and extracted with chloroform. The organic layer is washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with methylene chloride-methanol (99:1) is obtained 2.91 g of 5-(4'-ethoxycarbonyloxy-3'-methoxyphenyl)pentadienoic acid prenylamide.

Workup

  1. stirringthe resulting mixture is stirred at -10° C. to 0° C. for 3 hours
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with chloroform
  4. washThe organic layer is washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. washFrom the fraction eluted with methylene chloride-methanol (99:1)

Sources & evidence

ORD record
ord-22ee3cb605d04299a3a0f06bc4f64cff
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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