Triethylamine → HCID 66751353, Verbindung

HRID 535016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535016
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH2:19]([O:26][C:27]1[CH:31]=[C:30]([C:32](O)=[O:33])[O:29][N:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH2:19]([O:26][C:27]1[CH:31]=[C:30]([C:32]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:14][CH2:15]2)=[O:33])[O:29][N:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 136269673-(Benzyloxy)-1,2-oxazole-5-carboxylic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Produkt 1

HCID 66751353HCID 66751353, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (2.1 g, 7.2 mmol), 3-(benzyloxy)isoxazole-5-carboxylic acid (1.58 g, 7.2 mmol), triethylamine (2.79 mL, 20.0 mmol), EDCI (1.92 g, 10.0 mmol) and HOBt (1.53 g, 10.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 50:50). Solvent was removed to obtain a solid (2.2 g, 73%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 50:50)
  7. customSolvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-3e075fcd244f4327a2b5ea86be14b52f
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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