Phenylethanolamine → HCID 57495437, Verbindung

HRID 1039152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039152
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:11][O:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].ON1C2C=CC=CC=2N=N1>C1COCC1.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[NH:1][CH2:2][CH:3]([OH:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

6

Edukt 3

HCID 1000PhenylethanolamineHCID 757711-HydroxybenzotriazoleHCID 5541918-Methoxy-8-oxooctanoic acid

Produkt 1

HCID 57495437HCID 57495437, VerbindungAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide(EDC) (8.5 g, 44.3 mL) to a solution of 2-amino-1-phenylethanol (5.0 g, 36.4 mmol), suberic acid monomethyl ester (6.85 g, 36.4 mmol) and 1-hydroxybenzotriazole (HOBt, 5.0 g, 37.0 mmol) in THF (200 mL) at room temperature under nitrogen. Stir the mixture for 12 hours. Dilute the mixture with ethyl acetate (600 mL), wash with 1N HCl (2×150 mL), brine (2×150 mL), NaHCO3 (2×150 mL) and brine (150 mL) solutions and dry over sodium sulfate. Remove the solvent under reduced pressure to provide 7-(2-hydroxy-2-phenylethylcarbamoyl)heptanoic acid methyl ester (10.3 g, 91%), which is used in the following step without purification.

Aufarbeitung

  1. washwash with 1N HCl (2×150 mL), brine (2×150 mL), NaHCO3 (2×150 mL) and brine (150 mL) solutions
  2. dry with materialdry over sodium sulfate
  3. customRemove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8041fb1d28a240a39846c15891d0bf10
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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