N-Acetylserotonin → 3-[2-(acetylamino)ethyl]-1H-indol-5-yl 4-nitrophenyl carbonate

HRID 78693

Reaktionsgleichung

Reaktionsgleichung von HRID 78693
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].CN1CCOCC1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>O1CCCC1>[C:25](=[O:26])([O:27][C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=1)[O:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 903N-AcetylserotoninHCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformate

Produkt 1

HCID 867129853-[2-(acetylamino)ethyl]-1H-indol-5-yl 4-nitrophenyl carbonateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To N-acetylserotonin (0.9 g; 4 mmol) was added N-methylmorpholine (0.92 ml, 8 mmol), and 4-nitrophenyl chloroformate (1.61 g; 8 mmol) dissolved in tetrahydrofuran. Reaction was carried out for 0.5 h under an argon atmosphere. The solvent was evaporated. The residue was purified by column chromatography (SiO2, methanol/methylene chloride) to give 0.92 g (yield 60%) of crystalline yellow product with a melting point 153-156° C.

Aufarbeitung

  1. customReaction
  2. customThe solvent was evaporated
  3. customThe residue was purified by column chromatography (SiO2, methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-cb0d748909484c0fa6ac05719d52db41
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841453B2

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