Triethylamine → N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601993

Reaktionsgleichung

Reaktionsgleichung von HRID 601993
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].[CH:15]1([C@@H:21]([NH2:23])[CH3:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:15]1([C@@H:21]([NH:23][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:2]([F:1])[CH:3]=2)[CH3:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5325951(S)-(+)-1-CyclohexylethylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 57701210N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of 5 ml of ethyl acetate and 0.30 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.22 g of (1S)-1-(cyclohexyl)ethylamine and 0.20 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. 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 washed with hexane to obtain 0.37 g of N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 37 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
  4. washThe residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-2a5bf7b9c734421d8ef49376c9eceadf
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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