N-Acetyl-DL-alanine → Nalpha-acetyl-N-(2-hydroxy-4-methoxyphenyl) alaninamide

HRID 1888715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888715
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11].[C:12]([NH:15][CH:16]([C:18](O)=[O:19])[CH3:17])(=[O:14])[CH3:13].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C>[C:12]([NH:15][C@H:16]([C:18]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11])=[O:19])[CH3:17])(=[O:14])[CH3:13]

Komponenten

8

Edukt 5

HCID 7345N-Acetyl-DL-alanineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122101842-Amino-5-methoxyphenol Hydrochloride

Produkt 1

HCID 86660905Nalpha-acetyl-N-(2-hydroxy-4-methoxyphenyl) alaninamideAusbeute 9,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-methoxyphenol hydrochloride (5.24 g, 29.8 mmol), N-acetyl-D,L-alanine (3.91 g, 29.8 mmol) and 1-hydroxybenzotriazole (4.03 g, 29.8 mmol) in DMF (5 mL) were added triethylamine (4.15 mL, 29.8 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.72 g, 29.8 mmol), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate to methanol:ethyl acetate=1:4), and triturated with ethyl acetate to give the title compound (740 mg, yield 9.8%).

Aufarbeitung

  1. washthe mixture was washed with 1N hydrochloric acid, 10% aqueous potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by basic silica gel column chromatography (ethyl acetate to methanol:ethyl acetate=1:4)
  5. customtriturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-95c503edeeea4957b7bdf76588e45991
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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