Triethylamine → HCID 66696499, 화합물

HRID 929327노트

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HRID 929327 반응식
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.Cl.[OH:15][C:16]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20](O)=[O:21].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C=O>[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][C:20](=[O:21])[CH:19]=[CH:18][C:17]1[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:16]=1[OH:15]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 160436Serotonin HydrochlorideHCID 4466112,4-Dihydroxycinnamic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 66696499HCID 66696499, 화합물수율 51%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Serotonin hydrochloride (300 mg, 1.41 mmol) and trans-2,4-dihydroxycinnamic acid (253 mg, 1.41 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 (216 μl, 1.55 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 237 mg, 1.55 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI HCl, 297 mg, 1.55 mmol), and the mixture was gradually warmed to room temperature and stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (10 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (10 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 preparative thin-layer chromatography (PTLC, eluent: ethyl acetate-n-hexane=2:1, 0.01% formic acid) to give N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(2,4-dihydroxyphenyl)-2-propenamide (243 mg, yield 51.0%) as a viscous oil.

후처리

  1. temperaturethe mixture was gradually warmed to room temperature
  2. customThe solvent was removed under reduced pressure, water (10 ml)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted twice with ethyl acetate (10 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 preparative thin-layer chromatography (PTLC, eluent: ethyl acetate-n-hexane=2:1, 0.01% formic acid)

출처 및 근거

ORD 기록
ord-9dc49180f42a4750bb3e7c166c361bfd
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295624B2

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