Tetrahydrofuran → N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamide

HRID 601987

Reaktionsgleichung

Reaktionsgleichung von HRID 601987
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:21][CH3:22])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH:23]1([C@@H:29]([NH2:31])[CH3:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:23]1([C@@H:29]([NH:31][C:11](=[O:12])[C:10]2[CH:9]=[C:8]([O:7][CH3:6])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH3:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5325951(S)-(+)-1-CyclohexylethylamineHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 57701188N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamideAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5 ml of THF and 0.38 g of 3,5-dimethoxy-4-(2-propynyloxy)benzoyl chloride were added 0.21 g of (1S)-1-(cyclohexyl)ethylamine and 0.23 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.42 g of N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamide (hereinafter, described as the compound 23 of the present invention) represented by the formula:

Aufarbeitung

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37d67e90bc8147868db054ec37315321
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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