Triethylamine → HCID 66696497, compound

HRID 929330Notes

Reaction equation

HRID 929330 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:18])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[C:19](O)(=[O:31])/[CH:20]=[CH:21]/[C:22]1[CH:30]=[CH:29][C:27]([OH:28])=[C:24]([O:25][CH3:26])[CH:23]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C=O>[CH3:26][O:25][C:24]1[CH:23]=[C:22]([CH:21]=[CH:20][C:19]([NH:6][CH:5]([C:4]([O:3][CH3:2])=[O:18])[CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[NH:10][CH:9]=2)=[O:31])[CH:30]=[CH:29][C:27]=1[OH:28]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 445858Ferulic AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 24802218methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 66696497HCID 66696497, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

As mentioned above, 5-hydroxy-L-tryptophan methyl ester hydrochloride (350 mg, 1.29 mmol) and ferulic acid (251 mg, 1.29 mmol) were dissolved in a mixed solvent of dichloromethane (6 ml) and N,N-dimethylformamide (6 ml), and the solution was maintained at 0° C. To this solution were added triethylamine (198 μl, 1.4 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 217 mg, 1.4 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI HCl, 217 mg, 1.4 mmol), the solution temperature was gradually raised from 0° C., and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (20 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (20 ml). The ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml), and once with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: chloroform:methanol=3:1) to give 3-(3-methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-methoxycarbonylethyl]-2-propenamide (413 mg, yield 78.0%) as a powder.

Workup

  1. temperaturethe solution temperature was gradually raised from 0° C.
  2. customThe solvent was removed under reduced pressure, water (20 ml)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted twice with ethyl acetate (20 ml)
  5. washThe ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml)
  6. dry with materialonce with saturated brine (5 ml), and dried over anhydrous magnesium sulfate
  7. customMagnesium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. custompurified by silica gel column chromatography (eluent: chloroform:methanol=3:1)

Sources & evidence

ORD record
ord-d2b9f2f0e51141daba66265b61287d85
Source dataset
uspto-grants-2016_03
Patent number
US09295624B2

Reaction notes

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