Triethylamine → 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide

HRID 929332

반응식

HRID 929332 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:24]=[CH:23][CH:22]=[C:21]([OH:25])[C:17]=1[C:18](O)=[O:19].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[OH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[C:17]=1[C:18]([NH:13][CH2:12][CH2:11][C:8]1[C:4]2[C:3](=[CH:2][CH:1]=[C:6]([OH:7])[CH:5]=2)[NH:10][CH:9]=1)=[O:19]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 93382,6-Dihydroxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 160436Serotonin HydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 666965052,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide수율 14.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Serotonin hydrochloride (430 mg, 2 mmol) and 2,6-dihydroxybenzoic acid (312 mg, 2 mmol) were dissolved in N,N-dimethylformamide (25 ml), and the solution temperature was maintained at 0° C. To this solution were added triethylamine (310 μl, 2.1 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 346 mg, 2.1 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI HCl, 429 mg, 2.1 mmol), the solution temperature was gradually warmed from 0° C. to room temperature, 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, purified by preparative thin-layer chromatography (PTLC, eluent: ethyl acetate:hexane=3:1) to give 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide (93 mg, yield 14.9%) as a powder.

후처리

  1. temperaturethe solution temperature was gradually warmed from 0° C. to room temperature
  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 preparative thin-layer chromatography (PTLC, eluent: ethyl acetate:hexane=3:1)

출처 및 근거

ORD 기록
ord-ed6711017c25491fa26933f9ccd8f801
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295624B2

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