1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester

HRID 2089130

Reaktionsgleichung

Reaktionsgleichung von HRID 2089130
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([NH:11][CH2:12][C:13]([OH:15])=O)[C:7]=2[CH:16]=1.[C:19]([O:23][C:24]([N:26]1[CH2:29][CH:28]([NH2:30])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:19]([O:23][C:24]([N:26]1[CH2:29][CH:28]([NH:30][C:13](=[O:15])[CH2:12][NH:11][C:8]2[C:7]3[CH:16]=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:4]=[CH:5][C:6]=3[O:10][N:9]=2)[CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 58548759HCID 58548759, Verbindung

Produkt 1

HCID 674789043-[2-(5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetic acid (2.6 g, 9.99 mmol), 3-amino-azetidine-1-carboxylic acid tert-butyl ester (1.72 g, 9.99 mmol), EDCI (2.3 g, 12.0 mmol), HOBt (1.62 g, 12.0 mmol) in DCM (20 mL) were stirred at room temperature for 4 hours. The reaction was then partitioned between DCM and water. The aqueous layer was extracted two times with DCM. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, which was purified by silica gel column (hexanes:ethyl acetate 1:1) to afford the title compound as white foam.

Aufarbeitung

  1. customThe reaction was then partitioned between DCM and water
  2. extractionThe aqueous layer was extracted two times with DCM
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material, which
  8. customwas purified by silica gel column (hexanes:ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-97f377bbd18b4f32bdf663b3ad34a745
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436023B2

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