HCID 69818250, Verbindung → HCID 69818475, Verbindung

HRID 2417422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417422
C([N:8]([C@H:20]([CH2:34][OH:35])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][CH2:32][CH3:33])=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:32]([NH:31][C:29]([NH:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@H:20]([NH:8][CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:34][OH:35])=[CH:27][CH:26]=1)=[O:30])[CH3:33]

Komponenten

4

Edukt 1

HCID 69818250HCID 69818250, Verbindung

Produkt 1

HCID 69818475HCID 69818475, VerbindungAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]-N′-ethylurea (73 mg) in methanol (1.5 ml) was hydrogenated (1 atm) over 10% palladium on carbon (11 mg) at room temperature for 12 hours. After the catalyst was filtered off, the filtrate was concentrated and the residue was purified by column chromatography (silica gel, chloroform/methanol) followed by recrystallization from ehtanol/hexane to give N-ethyl-N′-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]-propyl]phenyl]urea (38 mg) as a white powder.

Aufarbeitung

  1. customat room temperature
  2. customfor 12 hours
  3. filtrationAfter the catalyst was filtered off
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by column chromatography (silica gel, chloroform/methanol)
  6. customfollowed by recrystallization from ehtanol/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f1aac32679234d3f9e962dbd6cba462a
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06826033B2

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