Triethylamine → N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester

HRID 1957027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957027
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)=[CH:9][CH:8]=1)[NH2:5].[CH2:19](N(CC)CC)C.[CH3:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[C:30](Cl)=[O:31]>O1CCOCC1.CCOCC>[CH3:1][O:2][C:3](=[O:18])[C@:4]([CH3:19])([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)=[CH:9][CH:8]=1)[NH:5][C:30](=[O:31])[C:29]1[CH:28]=[C:27]([CH3:26])[CH:35]=[C:34]([CH3:36])[CH:33]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 810883,5-Dimethylbenzoyl ChlorideHCID 572132553-[4-(3-Thienyl)phenyl]-alanine methyl ester

Produkt 1

HCID 67674849N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A stirred solution of 3-[4-(3-thienyl)phenyl]-alanine methyl ester (650 mg) and triethylamine (1.64 g, 11.8 mmol) in 1,4-dioxane (10 ml) is added 3,5-dimethylbenzoyl chloride (517 mg, 3.07 mmol) at room temperature. The mixture is stirred at room temperature overnight. The reaction mixture is diluted with ether and washed with 1N hydrochloric acid, sat. sodium bicarbonate and water. The organic layer is dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica with ethyl acetate/hexane (1:2) to give N-(3,5-dimethylbenzoyl)-2-methyl-3-[4-(3-thienyl)phenyl]alanine methyl ester.

Aufarbeitung

  1. washwashed with 1N hydrochloric acid, sat. sodium bicarbonate and water
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica with ethyl acetate/hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-95606a5704ec47e59b96bf3c5d9d6a1d
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780498

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