Diisopropylethylamine → 3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide

HRID 1881820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881820
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.Cl.[CH:55]([C:58]1[O:62][N:61]=[CH:60][C:59]=1[NH2:63])([CH3:57])[CH3:56]>CN(C)C=O.O>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([NH:63][C:59]2[CH:60]=[N:61][O:62][C:58]=2[CH:55]([CH3:57])[CH3:56])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acidHCID 684313035-(Propan-2-yl)-1,2-oxazol-4-amine hydrochlorideHCID 178484293HCID 178484293, Verbindung

Produkt 1

HCID 593312733-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution (15 ml) of 3-cyclopentyl-2-[4-(methylsulfonyl)phenyl]propanoic acid (2.00 g) in N,N-dimethylformamide were added N,N-diisopropylethylamine (3.49% mL), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo(4,5-b)pyridinium 3-oxide hexafluorophosphate (2.82 g) and 5-isopropylisoxazol-4-amine hydrochloride (1.15 g), and the mixture was stirred at room temperature for 48 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio) to give the title compound (2.50 g, 92%) as colorless amorphous crystals. MS: 405 (MH+).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-349fb371c7ef4f34b310e206ee6671d9
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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