1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,3,3-trifluoro-N-[(+/-)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide

HRID 10074

Reaktionsgleichung

Reaktionsgleichung von HRID 10074
[NH2:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8].[F:9][C:10]([F:16])([F:15])[CH2:11][C:12](O)=[O:13].OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[F:9][C:10]([F:16])([F:15])[CH2:11][C:12]([NH:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8])=[O:13]

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27779723,3,3-Trifluoropropionic acidHCID 21040236(+/-)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-oneHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 865976023,3,3-trifluoro-N-[(+/-)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

(±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one (128 mg, 1.13 mmol) was mixed with 3,3,3-trifluoropropionic acid in 2.3 mL of N,N-dimethylformamide. Hydroxybenzotriazole (17.4 mg, 0.11 mmol) was added followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol). The pH of the reaction mixture was adjusted to 8.5 with triethylamine and the mixture was allowed to stir at ambient temperature for 2 hours. Water was then added and the reaction mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, then dried (sodium sulfate) and concentrated to give the crude product. This was purified by silica gel chromatography to afford 120 mg (45%) of 3,3,3-trifluoro-N-[(±)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThis was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0300c97a88a5417abebd157852f56576
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091380B2

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