1-Hydroxybenzotriazole → 2-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide

HRID 425400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425400
C(=O)(O)[O-].[Na+].[C:6]([NH:9][CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[C:11]([OH:13])=O)(=[O:8])[CH3:7].[NH2:22][CH2:23][CH:24]([OH:31])[CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:6]([NH:9][CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[C:11]([NH:22][CH2:23][CH:24]([OH:31])[CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[O:13])(=[O:8])[CH3:7]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5172487AC-P-Bromo-DL-phe-OHHCID 55289824HCID 55289824, Verbindung

Produkt 1

HCID 667058552-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium bicarbonate (7.05 g, 83.8 mmol) was added to an ambient temperature solution of 2-(acetylamino)-3-(4-bromophenyl)propanoic acid (3 g, 10.5 mmol), 1-amino-4,4-dimethylhexan-2-ol (3.04 g, 21.0 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (4.02 g, 21.0 mmol) and 1-hydroxybenzotriazole (2.83 g, 21.0 mmol) in methylene chloride (105 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded 2-(acetylamino)-3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide.

Aufarbeitung

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bee873f249034be2987f610bf044608e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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